All The Single Ladies

Dating advice Archives

So your boyfriend (or girlfriend) still has a profile on an online dating site...

I've mentioned before about all of the other writers that I adore. Well that is why I am really excited to be involved in a fun new project with a large group of them.

Allow me to introduce the folks over at Met Another Frog, Alex of the Urban Dater, Feisty Woman, KB in NYC, Lena, Lucky Girl, Man Shopper, Mike Masters, Miss Melisa Mae, Nikki B, Simone Grant, Miss Taylor Cast, and Jackie Summers, who (along with yours truly) make up the members of The Insomniac Club.

Starting today, once a month, we will take one question and each post our thoughts on the subject. The goal is to open up dialogue and maybe even inspire a good healthy debate. Plus you might even discover another blogger to enjoy.

To keep up with everything just look for the hashtag #InsomniaClub on Twitter.

And now for the first topic:

You've just discovered you partner still has an online dating profile...

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Dating shouldn't be segregated


Yesterday I received a less than flattering comment through the contact form on my personal website. And while I am not a fan of those comments because they are a total blow to the ego that is not technically what this post is about but it's important to mention because it made me think and it's largely what has inspired this post.

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Stop making excuses

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About a month ago I wrote a guest post on That Happened To Me about a date that I went on. As you can read in the post, the date was pretty freaking awesome and it was the first time in quite sometime that I really wanted a second date. I mean truly wanted to see the guy again. But, the second date never happened even though he pretty much planned the entire thing with me.

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I won't give up on dating

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This guy looks like he's done dating

Throughout my life, many people have told me that I am a very positive person. I can find something positive in almost any situation in life. And yes, I will openly admit that sometimes it's a little annoying, maybe even a little sickening but it's just the way I have always been.

Honestly, I have no idea where it comes from. Trust me, my life hasn't been all rainbows and butterflies. I have had my share of heartache, troubles, and what have you (we all have). It's just somehow I see the other side I guess. I see how things could be worse or how things will get better. No matter what happens, I see something that makes it seem like it's not the end of the world. Granted sometimes it takes me a couple of days (or years), but nevertheless I still see it.

I was reminded of this positive attitude in a conversation with a friend the other day. We were talking about dating and all of the annoying and frustrating things we have had happen to us during our million years of dating. He is tired of all the bad things that happen and all the excitement over dates/relationships that fail in the end. So his answer is to just give up. He wants to just stop dating. And he asked if I had ever thought the same thing.

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If you don't want a second date then don't talk about it it

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The last couple of dates that I have been on have been pretty good dates. Actually one date was pretty awesome and fabulous and you can read about my thoughts on all of that over here. At any rate, the dates were pretty good and I sensed that the feelings were somewhat mutual since each guy mentioned what we should do on our second date.

Well, here it is weeks later and I have yet to actually have those second dates.

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Online dating messages gone bad: Ima stick it in ur...

A few weeks ago, I received what I believe is probably the tackiest message that I have ever received on a dating site. I was actually debating on if I should write about it because honestly I am not sure if I can talk about the message without being crude. And while I like being a sarcastic and maybe even a little witty on this blog, I tend to steer away from crude. That is saved for drunken Wednesday night dinners with my friends, you know where it's not written for the entire world to see (sorry mom).

At any rate, I talked with some friends just after I received the message and they all thought it was a little hilarious and quite tacky as well but I still wasn't sure. Well then, when I logged into OkCupid the other day only to see that I had received the exact same message it became clear to me that obviously I needed to write about it. I mean clearly the OkCupid Gods were telling me that I needed to, right?

Here is the exact message:

Subject line: Blank (apparently you don't really need a subject for this sort of thing).

Message: ima stick it in ur ass

I guess he kept it simple and went straight to the point, right?

Now, the first time he sent me this message I thought - how does a person respond to that sort of thing? I mean should I thank him for being so willing to stick "it" in that area of my body? Really, thanks buddy because not every guy is that into that sort of thing so I am glad that you are putting it out there just to make things clear.

I guess since he is sending me the message again he wants to make sure to get his point across. I get it, really, it's loud and clear. Though I am mildly concerned here, I mean there are no pictures of my actual ass on my OkCupid profile, so how does he really know he wants to stick it there? Not that I mean to sound like I am insulting myself or anything (I happen to think my ass isn't half bad) but how do you really know what you are getting into here?

Then, of course, the thought also occurred to me that maybe he just sends this message out to mass quantities of girls on a daily basis. But frankly that thought kind of scared me a little so I had to stop thinking about it.

Then an even worse thought came to me. What exactly is he planning on sticking there? I mean it's implied and we can all guess what "it" is. But to be technical he doesn't specifically say so I might need a little clarification here just to be sure.

I get that some guys (and girls) are just looking for that sort of thing. And let me just say, for the record, that I find nothing wrong with that at all. To each his own. By all means, really. I also appreciate brutal honesty so I guess I should thank him for that. Clearly I would not want to be out to dinner with him and have him drop a line like that just before they bring us the appetizers. I mean, talk about awkward, really. Though really, couldn't you have just simply asked me if I am cool with casual sex like everyone else?

Plus, I kind of feel like that sort of thing should be more of a question. Shouldn't it? I mean unless of course we are fooling around and you know for a fact that I am into that sort of thing. But that's not something you can really get from a person's profile on a dating site. Then again there was also a time that I didn't know a guy could pick up that I looked like a girl who was DTF (link to post) from a dating site either. So clearly I am the crazy one that is missing something here.

Trust me, I am super open minded about poor messages on dating sites. But really, I think this goes a little beyond a message that just doesn't thrill me all that much. I honestly can't see how any person can sit down to write a message and think "this will get me a date (or laid)". Clearly it got my attention but not in any good way. So even if you were looking for just a little romp, you failed buddy really.

Moral of the story? If you send me a message like this, I can think of plenty of places for you to "stick it" that aren't anywhere near me or my ass.

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Guest Post: A little something about decorum

Today I have an awesome guest post from my dear friend Dave Sorrell, also known as @rookiephenom on Twitter. I really love guest posts from guys because sometimes (or always) it's nice to get a little perspective from them. Now, we all know that I don't think there every guy feels the exact same way about things, but still it's nice to get their perspective.  Anyway, here he is talking about a little something called decorum.


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Single Woman TV: Breaking up during the holidays

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Breaking up sucks. There is really no other way to put it other than that. Actually, I am pretty sure that I have said it once or twice so I am sorry if it sounds like I am repeating myself.

Breaking up also sucks around the holidays because, well, it's a little difficult to know exactly how to handle it. Should you stick around to make it through the holidays or is it better to just end it?

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Advice for a reader: Should you give up on online dating?

Frustrated man hitting monitor screen on forehead

A little over a week ago I wrote a little advice for a reader who was curious to know if a guy was into her. Well, that same reader wrote again to ask my opinion on something else she is curious about - is online dating really worth it?

It seems as though she's had her fair share of bad dates and failed relationships with guys she has met off the internet. There was even a guy who told her that he felt there could always be someone more interesting to meet since there are so many potentials online. So even though he might meet a really awesome woman, he still feels tempted to respond when other women contact him.

It seems as though she is feeling a little beat up and wonders if there is a purpose to this whole online dating thing or if she should just give up.

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Advice for a reader: Is he that into me?

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I recently received an email from a reader asking for advice. She doesn't want me to share her entire email with everyone so I am just going to give you the gist.

She recently met a guy from an online dating site and they have been spending time together. However she is a bit confused due to the fact that he's openly admitted that he is divorced, meets other chicks from the dating site, and is really hung up on woman he met a few months ago who currently has a boyfriend. So she wants to know if he is interested in her or just wants to be friends.

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Could you date a guy who still lives with his parents?

Woman Dusting Houseplant

I love Sundays. Generally they are a pretty relaxing day for me. I drink a lot of coffee and write a lot. Sometimes I read and just try to relax. Actually, I am even known to cook a meal or two on Sundays. Another great thing is that Sundays are usually a great day for television, which is where I get to admit to watching some of the really lame shows that I actually watch.

I tend to be drawn to MTV occasionally on the weekends. There is often a marathon of shows like True Life or Made and what can I say, I am a fan of those shows for the most part. Hey it's a little better than my addiction to Teen Mom.

At any rate, earlier today I caught an episode of True Life which was about people who lived at home with their parents. I am pretty sure it's a fairly old episode of the show, but it's one that I hadn't watched before.

On the show there was a guy who was 30-something and still lived with his mom. He openly admitted to being a mama's boy and said he just hadn't had the desire to move out yet. He also openly admitted that he's never had a serious girlfriend and that he thinks it would be a little difficult to bring a lady friend home to his mom's house.

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In defense of the shy guy


Man in boxers crouching

Recently I made a new friend. I kind of use the term friend loosely here as I have been engaging in a little flirtation with him. Read that as I have been flirting my ass off. He knows it and it seems to be pretty mutual.

Anyway, upon getting to know this guy, he has openly admitted to me on more than one occasion that he is a really shy guy - actually to be technical here he is a shy guy who is also on the clean cut side. This is generally the kind of guy that I have a really hard time meshing with and I know it's a problem for other women too.

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I'm a real man and I don't play games

Side profile of a young couple playing scrabble

It seems like every time I am online looking through profiles on a dating site that I come across at least one guy that talks about how he doesn't play games or how he is looking for a girl that doesn't play games. This is something that I don't really understand.

First things first, some of these guys have a pretty awesome profile. I mean they talk about things they like to do and I feel like maybe this guy could be kind of interesting. But then, there it is "I am not looking for a woman who plays games" or "I am a real man. I don't play any games."

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A date shouldn't be treated like a job interview

Businessman in Meeting

A couple of days ago a reader left an awesome comment on my blog which really made me think. The comment mentioned how a lot of women treat a first date like a job interview which is something that I feel is true. It's something that I will openly admit that I have been guilty of in the past.

Honestly, I wish we could get past this idea that you have to be completely perfect on a date. When I first moved to Chicago, I spent a lot of time dating like that. I have to tell you it honestly wasn't any fun. I mean, one time when I met a guy for drinks the first thing that flew out of my mouth was a comment about how I sweat when I am nervous. Clearly that's not hot in anyway but I also don't think that sort of thing is really that big of a deal. And I am pretty sure that I don't want to date a guy that worries about something silly like that.

I used to beat myself up about things like. And as I was getting ready to meet a new guy I would always go through the list of things that I did wrong on my previous dates. It was exhausting.

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You have to pick up the phone once in a while

Young Man with Cell Phone

A couple of days ago I read an awesome post over on the Queer Guy Tells It Straight. The post was about text dating, in other words people who use texting as their main form of communication while dating. I honestly couldn't agree more with his post and it made me want to throw my two cents in.

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I don't want a guy who needs to be fixed

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I was chatting with a friend today about dating. He's a friend from Indiana who tends to get annoyed with the whole internet dating thing (hey, don't we all?) so a lot of times that's where our conversations lead.

Sometimes he feels frustrated when he sends a message to a woman and she doesn't respond. Forgive me here because I am paraphrasing since I don't remember the exact way he phrased it but apparently another friend once told him that maybe he's a little too put together. You know, it kind of goes with that idea that women want a man that they can change or fix.

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First impressions are exhausting

My niece and nephew came for a little visit this past weekend. We planned to go to the Museum of Science and Industry and the Lincoln Park Zoo. As we were getting ready to go on Saturday, my niece picked out what she wanted to wear. She chose a pair of black leggings with a pink and black striped sweater dress mainly because I was wearing black leggings and a black dress and she loves to wear outfits that match what I am wearing. She also decided that she wanted to wear the socks that I bought her when I was in NYC.
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Too much too soon: What's the point?

side profile of man sitting on a couch with his arm around a woman's shoulder

We've all met (and dated) the too much too soon guy. You know the guy that you go on a date with and he talks about all the things you guys can do together. He's incredibly complimentary but in a way like no other because he makes you truly think about the possibility of a relationship. And not just any relationship, but a relationship with him. You become hopeful, excited, curious.

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Does it even matter if there is someone out there for everyone?

Little Angel.jpg

"Dear God, please bring me a boyfriend this year"

I was having a conversation with a friend the other day about my frustrations with dating. It's been quite a run with me and this whole dating thing. Frankly I just get a little annoyed when everything seems to end up the exact same way. And while it's something I know I could never give up on (it's just not me to really give up on much of anything), I still have to say that sometimes I wonder if it's really getting me anywhere.

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I'm depressed I don't have your number

Invitation on a Slip of Paper

I have kind of neglected my OkCupid profile lately. It wasn't something that I did intentionally, it just really sort of happened. Though, I mean I feel like that seems pretty logical since I was busy planning my trip to New York and then I was actually In New York. Plus, we all know I have bad luck when I am busy and getting ready to go out of town.

Well, I came back and like any internet dating junkie I checked my messages. There wasn't really anything exciting there but while I was "online" I received two instant messages. One was from a fairly cute 22-year-old (the jury is still out on where I will go with that one) and the other was from a guy whom I have never met and haven't talked to in weeks for a few different reasons.

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Does your single status really say anything about who you are?



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I know I have written about why I am single many times before but it kind of seems like it's a subject that a person can go on and on about. There are so many ways to look at it and there are always new thoughts that come up. Let's face it, when you are single you almost always run into someone who wants you to have some clear cut reason for it.

Honestly the question annoys me because I don't understand why it always seems to come up. Why do people need a reason? It almost seems like people always want to diagnose that whole single thing - I mean there must be a reason for it, right? Never in my life have I ever heard anyone ask a person why they are in a relationship. So what's the deal with asking single people? I mean really, it's not that weird to be single is it?

One thing that really bothers me is when I start talking to a new guy and that is one of the first questions that flies out of his mouth. I mean forget what your favorite movie is or your hobbies. No, instead they want to know why I am single.

I can admit that sometimes that question spawns interesting conversations, like when a guy shares stories with me about his crazy ex-girlfriends. But more often than not I feel that question is used for some sort of judgment. It's almost as if people think the reasoning behind your single status will explain everything about you and will also somehow determine if you are relationship material or not.

It's like that question - when was your last relationship - which, coincidentally I am equally annoyed by. Does it really honestly matter when it was? Actually, I have to tell you I am more afraid of the person that tells me their last relationship was a month ago than the person that says 10 years ago.

Honestly, I have a couple of thoughts on all of this. First of all, you don't really want to know the real reason why I am single. I mean, let's be honest here if I have decided to stay single because I wanted to have sex with half the city, do you really (I mean really) want to know that?

What you really want is some kind of confirmation that I am not some psychotic bitch or assurance that I want a serious relationship. Which brings me to my second point - if you really want to know if I am relationship material then try dating me.

I have to tell you, if I am some crazy psycho who slashed my ex-boyfriends tires, I am surely not going to tell you that's why I am single. Likewise, just because I haven't been in a relationship for the better part of the past decade doesn't necessarily mean I am not relationship material. I mean maybe I have made some mistakes in my past and took time to learn from them. It also be that I wasn't ready for a relationship before and now I am.

Now sure, I am not going to deny that there are probably cases out there where the answers to these questions were spot on about what a person was really like and there are obviously some pretty sketchy reasons for a person's single status. But I will argue that it's not always the case. The reason for being single or the length of time that a person has been single doesn't necessarily tell you anything about a person. Plus it's really easy to sugar coat things (or flat out lie).

The fact of the matter is that people will tell you who they are if you really listen so how about just taking a little time (or you know, at least a couple of dates) and get to know them a little. That to me seems like such a much better and it greatly increases your chances of actually knowing what a person is like. 








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If a woman says she's not interested that means she's not interested

Man Laughing

A little over a month ago, I talked about the guy who threatened that he was going out with other women because I was too busy to meet him. Well, he is back. Actually, to be quite technical he's made a few guest appearances here and there over the past month

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Long distance relationships: Yay or nay?


High angle view of a businessman talking on a mobile phone and smiling Model Release: Yes Property Release: NA

Long distance relationships aren't for everyone. I've been in my fair share of them to know that sometimes they suck. You have to schedule time to be together and sometimes you miss out on stuff. And you have to rely so much on verbal communication because you can't be physically together when you want to be.

Sometimes one (or both) people involved don't even realize that they can't handle it until they're actually in a long distance relationship. When I was in college and moved to Indianapolis, I had a boyfriend. I think we lasted a month or two before things started to fizzle and ended with him telling me he just couldn't handle the distance because he didn't want to have to worry about when he would see me again. So even though I was fine with it and he assured me he was fine with it, he ended up bailing.

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In defense of the nice guy


For some reason I have been thinking about this whole nice guy thing lately. It could be that Mr. Google
appears to be a pretty freaking nice guy. But then again it could just be that I randomly think about things and then over analyze them to death. After all, that is what I do best as a writer/blogger.

When I was younger, I was way too into bad boys. I mean I was that girl that broke up with guys because they were too nice and then started dating the bad boys. I dated a guy that stole my parents' credit card, there was also a guy that didn't graduate high school and was heavily involved with some highly suspicious entrepreneurs (if you catch my drift). Half the guys I dated didn't have a driver's license because they were in trouble with the law in some fashion.

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I'm independent but that doesn't mean I can't be (a little) dependent

Young man helping a Young woman with a can opener

On more than one occasion I have had guys mention how there are certain characteristics they feel might keep me single. Then a few weeks ago at one of the ChicagoNow tweet ups, a friend asked me if I felt I had any habits or characteristics that I thought attributed to the fact that I am single.

There are things about me that I know certain guys don't like. I don't say that to make me sound bad or to imply I am a bad person. Honestly, I don't think that I am supposed to be liked by everyone and I certainly don't think that everyone has to want to date me. At the end of the day I just believe that people are who they are (though I am definitely not saying no one can change ever).

However, I know there is one thing that can be problematic at times. I want to avoid sounding completely cliché here, but the fact is that I am a very independent woman and tends to be a problem in the dating world. Though sometimes I feel it's because it often leads to so many incorrect assumptions.

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You like me but that doesn't mean you have to like everything about me

Mr. Google and I were talking the other day. Yes, that means he is still kind of in the picture. That is, as much in the picture as one can be when he is a few states away. Anyway, we were talking the other day when he said what I would like to call an over compliment. And it really made me think.

Here is the abridged version of the story. There are some not so flattering pictures of me on Facebook. I consider them not flattering because my hair is a much different color than it is now. Clearly I am totally going to out myself here, but no, the brunette is not natural. Honestly, I detest my natural hair color (on me). Mr. Google confessed that he discovered the pictures of me on Facebook and said that he thinks I look beautiful either way.

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Why can't we be friends?

Friendship Day with children and dog  

A thought occurred to me the other day - why do I seem to find so many guys that are opposed to being friends? I have had many conversations with guys, both from internet dating sites and just in general, and more often than not I hear things like "I'm not looking to make friends" or "I have enough friends already."

I'm not really even sure if I understand the phrase - I have enough friends. How is that really even possible? Are you really so popular that you have no room left in your life for another friend? I mean, you really can't even entertain the idea at all?

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Sometimes I am busy (Part 2) - I don't respond to threats


Man with laptop sitting on stool

Dating is frustrating (I am pretty sure I have said that before) and more often then not things don't go the way you want them to. Sometimes I think Saturday would be a great date night but the guy isn't available until Sunday. Sometimes I like guys that have no interest in me at all. And more often than I care to admit, I want what I can't have. We've all been there, but it's life and you have to deal with because let's face it there isn't really anything else to do about it.

I came back to the city earlier this week. Actually I came back a day later than I thought because there was a little mishap with the train schedule. Needless to say I was tired, a little cranky, and was really just ready to be home. Of course Mr. Doesn't Understand That I am busy that I talked about in my previous post started in with his spiel about how he really wants to meet me and so on.

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Sometimes I am busy (Part 1)

Shadow of annoyed woman at computer

The fact that I tend to be a pretty busy girl is pretty well known to anyone who knows me. This is not a fact that I hide or sugar coat from guys when I first meet them. There are times when I don't have that much on my plate and other times when my plate is full everyday. I've always thought this is pretty normal for the life of a single woman in the city.

Now, before I go any further, let me make it clear that I genuinely try to make time for dating. And if I meet a guy I want to seriously date I will definitely make time for him in my life as well. But do I really feel the need to keep a few nights open just in case I get a date? Probably not.

With that said, obviously this can be a problem when I am trying to set up a first date with someone. As hard as I try, sometimes it's just not possible to set up something for a few days and in some cases it might have to even wait a week. I don't say that to come across as some kind of superficial bitch or to imply that my life is anymore important than anyone else's because I definitely don't feel that way. All I genuinely ask for is a little patience when this happens, especially when I am being upfront about it and when I would do the same thing if the situation was reversed.

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Just because I don't want to sext doesn't mean I am a prude

Fuzzy Handcuffs.jpg

It's really no secret that I meet guys off the internet, therefore it's not all that shocking that I also give one my number from time to time. Honestly, I have to say that I am not overly excited when I give a guy my number only to have him text me in return. Call me crazy, but I think if you ask for my phone number then you should just pick up the phone and actually call me. However, it's not really a total deal breaker so I tend to just let it slide.

Texting with a new guy generally starts out pretty simple with questions about my day or what I am doing that weekend and so on. This is all fine and dandy to me. However, sometimes the personal questions start to slowly creep in and he's all interested in my favorite position and the craziest place I have had sex. Then, the conversation totally takes an even bigger turn and next thing you know he's talking about how horny he is and asking if I would like to help him out. Followed by a very through and explicit description of all the things he wants to do to me. And all I am left thinking is how did this happen? How did we get from talking about going to see my sister to you asking if I'd like to see a picture of your penis?

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Some guys should be banned from sending me messages online

Man typing on laptop

I haven't really given my profile on Plenty of Fish a whole lot of attention lately. Honestly, I am not sure if I have this fantastically brilliant reason as to why that is the case, that just seems to be the way it's been happening lately.

So it seems only logical that I was a little surprised the other day when I received an e-mail alert that someone had sent me a message on there. I tend to get a little excited when someone sends me a message from an internet dating site. That's totally normal right? I guess it's just the excitement of possibilities and, I mean, let's face it, who doesn't like the idea of someone thinking they are attractive?

At any rate, I logged on to read the message and was even more surprised because I immediately recognized the guy's picture. He is someone that I met and went on a couple of dates with when I first moved to Chicago. I can't recall the specific details about our encounter, but I do remember being a little interested in him. That is, until he fell off the planet only to resurface a few months later claiming he really liked me and made a huge mistake but only to fall off the planet once again.

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I would like a date that knows how to use grammar correctly


I'm going to make a really huge and personal confession here. I am a grammar and spelling whore. Yes, I said it and it felt good and no I am not ashamed. Translation? It's a pretty necessary thing for any guy I date to know basic grammar and spelling. Now, this might seem like it's not that big of a deal or really all that hard to find but trust me it is. And anyone that has ever dated on the internet can vouch for me.

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I'm bored so do you want to go out?

Bored man waiting at table in restaurant

We've established that some guys need to learn what a date really is (and also a better place to meet women off the internet). Well, I kind of feel like we need to go into this whole asking a girl out on a date thing. I am just going to get straight to the point here, the words "I'm bored" should never be followed by "would you like to meet" (or any other derivative of that).

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Sitting on my couch is not a date

Destroyed couch

I've had a epiphany this week. Actually, back up for a second. Technically I have been thinking about this for a while, I just feel like it was fully confirmed this week. If you read my blog, you know that I am pretty open minded when it comes to dating and by no means am I a prissy princessy kind of girl. I have to be honest here though guys, sitting on my couch (or your couch) is not a date. Really, it's not.

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Guest post: you want my phone number or what?

It's time for another guy to guest blog on dating rules. This time we have a post from Dennis Frymire about that whole "you have to wait three days to call a girl" rule.

Woman offering piece of paper with her phone number
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Here's a tip for guys filling out a profile on an internet dating site

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Here is the correct way to take a picture of yourself

Earlier today I was perusing through the profiles on OkCupid and I kept noticing one thing that really annoys the crap out of me. Obviously since I am no stranger to the world of online dating this is not the first time I noticed this annoying thing. Though today I seemed to notice it more (or maybe I was just irritable today). So I thought I should give a little tip for all of the guys out there filling out a profile on an internet dating site. Lose the picture of you in the mirror holding your phone.
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Guest post: Don't be too available dammit

Since I have such a fun time talking about all the dating rules (and how much I think most of them are crap), I feel kind of like I need a guy's point of view. So I've asked some of my most favorite guy bloggers to tell me what they think about some of them and over the next few weeks I will be posting their thoughts. First up is Alex from the Urban Dater (a very awesome website about dating and relationships) who talks about being too available, or as he's titled it "Don't Be Too Available Dammit!".

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The 22-year-old approach to picking up an older woman

Student Asleep During Lecture

Will someone please tell me what the deal is with 22-year-old guys? Seriously, their approach to picking up women (mainly older women) just flat out sucks.

Anyone who knows me will tell you that I am not overly fond of guys that are younger than I am (actually I am not overly fond of guys my age either). I tend to be into those that are more in the 32 to 35 age range - with an even bigger preference for those that are even older. Honestly I have no idea why this is; it's just how I have always been. Clearly I would love to say it's because I have better luck with older guys, but I am not really sure if I can say that.

Point being that there is a pretty big age difference between 22 and 32, especially in man years. So yes, I get that it's an age thing. Though, it's something that seems to be a trend which makes me wonder. And I mean, even if it is a 22-year-old is it too hard to ask for a little respect here?

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It's not giving up it's just moving on

Man sitting in back of van holding cup, low section

Anyone who knows me will tell you I am a pretty impatient person, I always have been. I am the type of person who likes to get things done and I always go after what I want. It's part of what brought me to the city - I need the hustle, the noise and all it's craziness. These are things that just seem natural to me, it's who I am. Sometimes I wonder, though, if it makes me give up too easily.

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Standards vs. rules in dating

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My friends sometimes think I am too open-minded; I often think they are crazy. I have always been a person who doesn't like to play by the rules, just ask my mother and my sister. It seems so easy to miss out on life when you are so busy worrying about the list of things you should be doing. Though, I have been noticing lately that this can be a problem with it comes to dating. And it's important to remember there is a huge difference between standards and rules.

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Please meet me in person before inviting me into your bed

man sits on the bed in de sleepingroom

A little while ago a friend wanted to fix me up with another friend and all the guy could talk about was having me over to his place. And he wasn't talking about cooking me a little dinner and playing some trivia on the Wii (read that as he just wanted to have sex with me). I guess he's had an issue with some women that are just too attached after the first date. So he's not to keen on the whole date thing. Apparently now he is punishing all women, including me.

This is not the first time I have been in this kind of situation.

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Sometimes dating different types isn't really all that different

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Everyone knows by now that I am a huge advocate for dating all different types of guys. I genuinely feel that when you only date certain types of guys that you just limit yourself way too much and might miss out on something really fantastic.

Whenever a guy asks me what my type is I always answer that I don't have one because honestly I am not sure if I do. I tend to not get caught up in labels and honestly I want to focus on getting to know a person rather than worrying about what "type" he is. However, I have started to notice something lately. Even though I date a variety of guys they all seem to have one thing in common with each other - they're unavailable.

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A cattle call won't ever get you the girl

2 cows in a pasture

Last night, I read a fabulous post over on The Queer Guy Tells It Straight. The post was about men trying to pick up women from their cars and how this attempt doesn't ever (and really definitely shouldn't ever) work.

I have to say that he is completely right here, fellas. In fact, I would say that, as a woman, I don't find anything even remotely flattering about a man who does this. If you are a woman who thinks this kind of behavior is flattering you seriously need to check your standards on how you feel a guy should treat you.

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Sometimes it's not a deal breaker, it's just down right picky

View of a young man picking out shirts from his wardrobe
The other day I was sitting on the bus on my way home from work and there was a girl next to me reading a magazine. I have no idea what magazine it was but there was a section about deal breakers in dating for women.
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You can't teach an old douche bag new tricks

Man with present standing between two women

On Sunday night, I caught the first episode of the new season of Tough Love. We've already established that I am a big fan of the show; in fact I actually want to be on it. Anyway, this season is actually tough love for couples.

While watching the show, I kept thinking to myself - are you kidding me?

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Let's be exclusive friends

Man Leaving an Apartment Building

A little while ago, I had the most interesting conversation with a guy on OKCupid. Everyone knows that interesting actually means to weird or puzzling which generally translates to blogging. So here we are.

It went a little something like this (I didn't change this conversation and I am really sorry it's so long, but as you will see I needed to include it all):

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I think it's time to define relationships

Young couple lying in bed

Relationships are tricky and generally, what works for one person doesn't necessarily work for another. Let's face it, dating will never be that cut and dry. Which is why I am a firm believer that people should define their own relationships. There are, however, certain core ideas that make up different kinds of relationships that are usually the same across the board. After many conversations with various people I have met, I have realized that many people really don't know the difference between these types of relationships

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Breaking up is hard to do, but just do it already

Sad Woman Turning Away from Man

I had a conversation with a friend the other day who was about to end things with a girl he was seeing. He said he wasn't really sure how to do it and that the whole situation was making him feel like a total ass. Which we all know really made me think and thinking leads to writing and here we are.

So, tell me something here. Why is it that guys feel like such an ass when breaking up with a woman?

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Just because he's ending it doesn't mean there is anything wrong with you

Man and Woman Talking in Cafe

Break-ups are tough. No one really likes to hear that someone they like doesn't want to date them especially when you think things have been going just fine. So why is it that when we are getting dumped that we tend to make things even harder on ourselves by picking at all of our little flaws?

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Please do not check out other women on a date


Anyone that knows me really well can tell you that there are certain things about my life that I am super anal about. For instance, I fold my towels all the same way and they are organized on the shelf by color. It's my system, always has been, and I don't like it when people mess with my system. When it comes to dating, however, I tend to be pretty laid back and open minded.

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Dating is a privilege not a right (part 2): You are not a princess


The other day, I read an awesome post from Single City Guy called Women Aren't Entitled to Anything which really made me think about how there are some women that feel they are entitled to certain behavior from men. You know, the whole idea that men should pay for everything, buy them gifts all the time, and generally worship the ground they walk on. I like to call this the princess behavior.
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Dating is a privilege not a right (part 1)

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Let me start by saying that I am talking about both women and men here. You can call it my little disclaimer if you will, but I really feel this is a principle that applies to both sexes. Not that I am perfect (trust me I will be the first to name all my flaws if you ask me), but I personally feel pretty special when a guy I like wants to date me. So in return I like to try to show that as best I can.

When you first meet someone, they are generally pretty sweet and try to impress you, which generally continues at least through the first few dates. Sometimes, however, this nice thing stops and is replaced with the person's unwillingness to admit they like you. This generally happens because the person gets comfortable with the idea that you like them which then develops a cocky attitude. You know the whole idea that you like them so they can do no wrong.

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If he doesn't want to ask you out, try making him jealous (Really?)

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I have started reading a new dating book called Date Like A Man by Myreah Moore and Jodie Gould. So far the book hasn't been that bad but then again, I am only 40 pages in. The main idea about the book is just what the title suggests, telling women how to "date like men." Basically the theory is that since men have so much fun dating (and aren't dead set on finding a partner for marriage) that women should date this way too.


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Why women shouldn't jump to conclusions...

I found this the other day on YouTube. Now, I have to say that I am not entirely sure if it's real. Though I also have to say that I have known women like this so it wouldn't shock me if this did actually happen. It's a great example of why women shouldn't jump to conclusions. You know the whole idea that if a guy doesn't call you at a certain time then he must not be interested, a jerk, or any other insult you can think of (something that I will talk more about later).

Is it strange that he didn't call her on his trip? Probably.

However, I will say that I would think that if you hadn't heard from your boyfriend in a few days you would be more worried about his safety and well being (you know, being his girlfriend and all). Which is why this is quite entertaining and why I say women should be careful when they automatically assume a guy is a jerk.

Sorry it's a bit long. It's highly entertaining, I promise.

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Always try to keep an open mind when dating


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Let me start off by saying that I am not a big fan of The Bachelor/Bachelorette. Honestly, the idea seems completely ludicrous to me. I mean come on. You group the "beautiful" people together at some insanely gorgeous location then send them on dates with helicopters, waterfalls and exotic (read that as expensive) foods. Then, in the end, you choose the person you want to marry, probably propose, and then venture out into the real world to make it work.

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What's so bad about going to a strip club with a guy?

Sexy Stripper.jpg

If you've ever picked up a Glamour, you know they usually have a section about dos and don'ts. They provide a little entertainment/humor and are really just those little useless facts that might come in handy on your next trivia night. Well the other day I was browsing through the magazine and read that 69 percent of readers say going to a strip club with a guy is a don't.

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Guest Post: Okay guys, it's time to break up with Ed!!!

Sometimes gay guys have the best views on straight guys. My dear friend, Daniel Scogin, definitely falls into that category. I know it might seem like I am a little biased, but I promise he really does. When he asked to guest blog of course I accepted (and by accepted I mean encouraged). We are actually thinking about starting a little series, so be on the look out for that. Here is his first post where he encourages guys, in a very non-subtle sort of way, to ditch Ed Hardy.

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Who cares who asks who out on a date


Dating is already confusing enough and this whole idea of who should ask who out honestly just makes it worse. I continually read about it in every dating book that I pick up. The consensus essentially is that if you are a woman, you should never ask a guy out. Sure, you can hint around to it and try to convince a guy to ask you out. However, you should never actually ask him out.

This is a concept that I honestly don't understand. I mean did I miss something here, it is 2010 right? With everything else that is evolving in the world, why hasn't this?

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Guest post: Learning happiness


Egg Smiley Face.jpg

A couple of weeks ago I had a guest blogger named Samantha Karlin who wrote about how to write an online dating profile.

I have invited her back, this time to talk about how to be happy and content. Even more importantly, how to have a great outlook on things even if living the single life gets you down.

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Don't act like you don't care about sex on the first date

Do not hump.jpg

Sex on the first date. This really isn't breaking news here. I mean, there is really nothing new about this dilemma. While obviously I don't know for sure, I am pretty sure it's been around since the whole concept of dating was invented.

Every dating book that I have ever read that talks about sex on the first date says it's a bad idea. Many guys I have talked to/dated say it's a bad idea. I would say it seems as though the consensus is that it's a bad idea.

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The great date in Chicago: This week's spots around town


Planning a date in Chicago can be a little overwhelming. Let's face it, with the 999 events the city has going on at any given time it's hard to know what to choose.

Well, I have decided to help a little here. Every Wednesday I'll give you some events/ideas that are going on around the city that are sure to make a great date. Anything from great restaurants, to comedy shows, to concerts and festivals. You name it. I'll also include some budget friendly events because just because we are in a recession doesn't mean you can't get out and have a great time (and impress your date).

Also, if you have events that you know of please feel free to share with me by emailing me here.

Happy dating!!

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Have you ever double booked?

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Lately, I have heard a lot about double booking dates. The subject came up on a few shows and movies that I have watched lately. Then the other day I saw a couple of posts about it on Twitter.

If you don't know what double booking means, essentially it's having two dates back to back in one day. Now, I have to say that I personally have never double booked. Though I can't say it's because I think it's wrong, it's just simply because I have never found myself in that situation. Generally if a guy asks me out and I already have a date I tell him that I am busy and try to plan something for another day.

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Five traits I never knew were deal breakers

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A new book has surfaced which could make quite a few single women rethink their dating strategy. Marry Him: The Case for Settling for Mr. Good Enough by Lori Gottlieb hit store shelves yesterday and it's actually causing quite a controversy. The book is about exactly what the title suggests - women settling for "Mr. Good Enough" instead of holding out for "Mr. Perfectly Right."

I will admit that, as a single woman, I find the title of the book really hard to swallow. Honestly I think if I was a man I might have a few issues with it too. Since I haven't read the book I feel it's a little tacky and unfair to really critique it in anyway.

Though, my curiosity has been piqued, which of course led me to do a little research on the author and some of her ideas.

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Guest post: The ABC's of a good online dating profile

Mouse Love.jpg

I have talked a lot about internet dating. While I am really no stranger to it (you've seen some of the bad messages and heard my stories about a few guys I have met/talked to from various dating sites), I recognize that it's new territory for a lot of people out there. Plus let's face it, no matter how experienced you are, a person can always use a few more tips right?

Samantha Karlin is the Dating Diva for an online network called Meezoog. Here she gives advice to online daters and fellow singles. She has offered to do a few guest posts to offer her expertise with online dating. This week, she's offering tips on how to write a snazzy online profile.

If you haven't heard of Meezoog you should definitely check out their website. There is also some additional information with Samantha's post.

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Guy proofing your apartment: More of the worst dating advice ever

A little while ago, I wrote about a little book I like to call The Cookie Cutter's Guide to getting the Cookie Cutter Guy. As a little refresher, the book is called Why Hasn't He Called?

I have found yet another thing that I was not aware I should be worried about while I've been dating - guy proofing your apartment. This book offers a good 15 pages on the subject. Who knew there was that much information? Honestly, I didn't think that guys really paid that much attention to my apartment. And I have to say I think it's pretty tacky for a guy to completely chuck me for any one of these reasons.

The funny part about all this is that they claim that your apartment should be a reflection of who you are. Kind of sounds more like it's a reflection of the woman you want him to think you are. 

I would also like to add here that the authors themselves admit that this was not the case for them (they are a married couple). In fact Matt even said that when he first went to Tamsen's place he couldn't believe what he saw - dirty clothes, no furniture and boxes of stuff everywhere. Yet none of this made him run. Later in the night he found out that there was an explanation for all of it. She was in a transitioning phase. He also admitted that if he hadn't been so into her he might have bailed.

Correct me if I am wrong here, but doesn't this kind of negate their whole theory on guy proofing your pad? Actually I am pretty sure it backs up the idea that what your apartment looks like might have nothing to do with it at all. Maybe it actually might depend on the guy's level of interest. Genius really.

Here are a few of my "favorite" rules and suggestions (and by favorite I mean laughable. I don't condone following these at all). Would any guys out there like to offer their opinion on any of these?


Gallery sneak peek (8 images):

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Should I keep seeing him?

Couple of frogs.jpg

I received an email the other day from a woman I know who is having a little dilemma with a guy she's recently started seeing. Here is the gist:

She met a guy through mutual friends and they immediately hit it off. A few days later they met for a quick drink and then that weekend they had their first "formal" date. Though he ended the date with a kiss she seems a little thrown by him. First, he asked her out via text, which is a huge no no in her book. Second, he didn't offer to pay for any of the date at all. Essentially she isn't sure if she should keep seeing him or not.

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