All The Single Ladies

Must be a guy thing Archives

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

user-pic
Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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.

Continue reading...

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

user-pic
Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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."

Continue reading...

You have to pick up the phone once in a while

user-pic
Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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.

Continue reading...

Tips when unfastening a bra

user-pic
Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Woman putting brassiere on

Last week, at the ChicagoNow tweet up, I was talking with the lovely ladies from Chicago Hearts Trivia and the awesome Elliott from Geek To Me. I am not sure exactly how it came about (though I am pretty sure it had a little something to do with my trivia question) but somehow we ended up having a whole conversation about unfastening a woman's bra. That is, we had a whole conversation about how some men are painfully awful at it.

Continue reading...

A relationship should be 50/50

user-pic
Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

close up side view of young man and young woman sharing drink
The other day I was having a conversation with a friend about relationships. I am not sure exactly what I said, but something made him mention that he felt the man should be the dominant one in the relationship. This kind of caught me off guard and I wasn't sure if he was being sarcastic or cute and clever. Turns out that is the way that he genuinely feels and I am not really sure why but that just seems a little strange to me.
Continue reading...

A relationship should be 50/50

user-pic
Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

close up side view of young man and young woman sharing drink
The other day I was having a conversation with a friend about relationships. I am not sure exactly what I said, but something made him mention that he felt the man should be the dominant one in the relationship. This kind of caught me off guard and I wasn't sure if he was being sarcastic or cute and clever. Turns out that is the way that he genuinely feels and I am not really sure why but that just seems a little strange to me.
Continue reading...

Too much too soon: What's the point?

user-pic
Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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.

Continue reading...

Why aren't there any oral sex classes for men?

user-pic
Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

legs.jpg

I've seen countless information on oral sex classes for women. Don't get me wrong here, I am not knocking these classes in anyway, because I see nothing wrong with them. Actually, I have never even been to this sort of class so I really can't offer my opinion either way. There is one thing that has me stumped though - where are the oral sex classes for men?

Continue reading...

It's called having sexual confidence

user-pic
Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Fishnet stockings

The other day, I was talking to a friend that I have known for a while. He doesn't live in Chicago so really we mostly trade e-mails back and forth. Occasionally his e-mails involve something to do with my blog since he reads it fairly regularly.

Anyway, we were discussing how some guys choose to approach me when they are "hitting" on me. He advised that I should be aware of my confidence and sexual aura (actually he flat out said to be careful how I use it). And also talked about how I blog about sex so maybe some guys get a certain idea about me.

I am not so sure how I feel about that. Actually, I entertained his ideas for a few moments and then thought to myself are you kidding me?

Continue reading...

In defense of the nice guy

user-pic
Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Sweet.jpg

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.

Continue reading...

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

user-pic
Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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.

Continue reading...

We are human beings, not porn stars

user-pic
Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Lovers Undressing

I am going to make somewhat of a confession here - I have been known to enjoy watching an occasional porn or two. And honestly I am not saying that to shock anyone because I think it's a pretty normal and natural kind of thing. Porn can be a pretty fun and even a pretty useful sort of thing, but all too often I think it's easy to forget that porn was also created for entertainment purposes.

Continue reading...

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

user-pic
Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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?

Continue reading...

What will it take for men to go to singles events?

user-pic
Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Today's blog is a little something different, but that is because I am legitimately curious about something. So I am hoping all the single guys out there can help me out. Why is it that so few single guys go to singles events?

Group of men
Continue reading...

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

user-pic
Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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).

Continue reading...

Sitting on my couch is not a date

user-pic
Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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.

Continue reading...

Here's a tip for guys filling out a profile on an internet dating site

user-pic
Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Thumbnail image for Thumbnail image for woman taking picture with cell.jpg

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.
Continue reading...

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

user-pic
Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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?

Continue reading...

Using a crutch for sex is probably not your best laid plan

user-pic
Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Man with crutch

We all have our staples when it comes to sex. A lot of women tend to have underwear or something that makes them feel sexy. Men sometimes do a couple of push ups when you are in the bathroom so they feel a little hotter. Those things I get. However, I have never in my life met a man that uses his apartment (or anything in it) as a crutch for sex.

Continue reading...

A cattle call won't ever get you the girl

user-pic
Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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.

Continue reading...

Please do not check out other women on a date

user-pic
Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

ThisIsTheLife.jpg

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.

Continue reading...

Don't worry if he cheats, he just might have a low IQ

user-pic
Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

ISHERB_Caveman.jpg

Cheating, so easy even a caveman could do it.

There are many theories on why men cheat. Some say it's just their nature; some say it's lack of satisfaction; some say they just cheat. And yes, I promise I know women cheat too. I found an article in the Telegraph (a publication in the UK) the other day which could throw yet another reason out there.

Continue reading...

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

user-pic
Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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.

Continue reading...

Ladies, please lose the stache

user-pic
Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

As a single woman, I don't personally have a guy's perspective on pet peeves about women. So that's why I rely on guys to give me their opinion. Since I write about all my little pet peeves about guys I figured it's only fair that I write about the ladies too. Which is perfect since there is a guy I know who's been asking me to write about something women do (or technically don't do) that really gets under his skin.

This little thing is facial hair, actually it's mainly the mustache. Now, clearly I did not know this was an issue but apparently he's been on several dates where it has been. And sure enough, I have talked to a couple of other guys who said that they have noticed the same thing. Honestly, I didn't really know that guys noticed that kind of thing but apparently they do and apparently they don't find it attractive.

And sure, I know. It seems like a little thing so why can't a guy get past it? Well, let's face it, as women we also have little things that we can't get past either. In fact, when I wrote for examiner.com, I wrote a whole article about why guys wear socks during sex. Everyone has something so I feel this little thing is definitely fair and valid. And I mean come on, this is a pretty easy and cheap thing to fix.

So ladies, lose the stache. Here are some products that can help you do it.

Gallery sneak peek (10 images):

View the gallery...

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

user-pic
Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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.

Continue reading...

Man gets penis stuck in steel pipe

user-pic
Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Not sure what the appeal is here. Ouch.

Word on the street is that a man in the UK got his penis stuck in a steel pipe the other day. No one really knows exactly how since the man declined to tell anyone how it happened. Though logically I think it is hard to believe that this was an accident, so who would really admit all the details?

 
Here's the kicker to the whole thing. It took firefighters seven hours to actually get the penis out of the pipe. Apparently it had become too aroused from lack of blood flow. Sounds like a pretty tricky situation to me. The penis ended up with a few bumps and bruises but is otherwise fine. At least the story has a happy ending, right?

The 26-year-old effect

user-pic
Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

 

Douchebag.jpg

Not sure if this guy is actually 26 or not

I try not to generalize people at all because I truly believe in the whole "to each his own theory." Hello, I am a Sociologist who learned that the world is one big salad bowl and I truly believe this as well. When it comes to dating, I try to be the same way. You have to at least know a little bit about a person before you can say you aren't interested.

Continue reading...

And the winner of the Name the Penis Contest Is...

user-pic
Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

A couple of weeks ago I wrote about my examiner friend Michele Gwynn who was asking all the ladies out there to participate in the Name the Penis Contest.

The winner was announced last week. Click here to find out.

Show him a little skin, it's not a sin

user-pic
Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

According to a recent study women who show 40 percent of their skin are more likely to attract a man. This shouldn't seem all that shocking since men are visual people who appreciate seeing a little skin on a woman. Though, I will admit that I feel like 40 percent is kind of a lot. I mean that is close to half of my body.

 

The study counted each arm for 10 percent and then each leg was 15 percent, the torso was the remaining 50 percent (apparently your head doesn't really count at all here). If you wear a dress, essentially you have your 40 percent right there. So really, I guess that doesn't seem all that bad.

 

Be careful though ladies, because apparently if you show more then your 40 percent that will actually turn a man off. Apparently when you reveal too much it makes a man suspect that you are unfaithful. Yes, that's right, too much skin makes a man think you are one cheating floozy. Talk about stereotypes. Clearly I get that if you show too much skin that you can give off a slutty vibe. However, I don't think that's really an indication that you cheat.

 

I also have to say that we live in Chicago and I am not really sure how well this whole percentage theory stacks up against the winter here. Sorry guys, but hanging my 40 percent out when it's 30 below zero is not really my idea of fun. So I think I would have to save that for a night in. Hopefully you can cut me a little slack there.

 

Gallery sneak peek (6 images):

View the gallery...
Continue reading...

Introducing the Name That Penis Contest

user-pic
Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Have you ever noticed how amusing men find it to name their little buddy down there?

My friend Michele Gwynn who is the San Antonio Sex and Relationships Examiner for examiner.com and Kat McCarty, of "Thing of it is" blog, are sponsoring a Name That Penis Contest. One lucky winner will win a fantastic sexy gift basket.

I am inviting all you Chicago ladies out there to join in the fun. Click here to find out more information about the contest including how you can enter to be the winner.

If you want to see some of the great reasons why men think of these names, check out Michele's article here.

Continue reading...

Most Active Pages Right Now

ChicagoNow.com on Facebook