All The Single Ladies

Sex Archives

Match.com releases new study on singles

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Jessica Downey

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

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Recently a research firm conducted a survey for Match.com about the behavior of singles. They surveyed more than 5,000 men and women and I have to say that I found the results to be pretty interesting. Now, let me just say that I tend to be pretty skeptical of statistics. So I know that this doesn't mean that every woman or man out there does or doesn't feel this way but never the less, I found the findings to be interesting.

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Should you make a guy work for sex?

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Jessica Downey

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

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I read an article the other day and for the life of me, I can't find where it was that I read it but it talked about having sex on the first date and how it's too soon and so on. Clearly that is not really that uncommon of an idea, I mean I have read that in countless books and articles. But somewhere in the article it mentioned how a woman should make a man work for it. Coincidentally I have had conversations about this with a couple of guy friends I know lately so apparently there are quite a few people that share this belief. 

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Date Night Challenge Week 2: The birthday party

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Jessica Downey

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

a young woman sitting on the bed and trying on lingerie

I have finished up the second week of the Date Night Challenge. My birthday was last weekend and there was a big party thrown in my honor. I also spent a lot of time with my mom before the big day because, well, I am her baby and that's what mom's like to do before their baby's big birthday. So that meant I didn't really have time for much dating and there's been a lack of awesome guys to date in my life lately.

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Paid dating sites vs. free dating sites

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Jessica Downey

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

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This guy looks really serious. I wonder which dating site he is browsing.

A couple of weeks ago I had the opportunity to meet Sam Yagan, the CEO of OkCupid for breakfast. We had a pretty fantastic talk about dating, specifically online dating. Seems logical right? I mean what else would the CEO of an awesome dating site and a dating blogger talk about?

We talked a lot about OkCupid and other dating sites and he asked some of the things I like about OkCupid. Aside from the fact that I seem to find some amazing blogging fodder from the site (aka the DTF guy and the guy who offered me free pie), I also said that I like that there is an instant messaging service because I feel like you can weed out creepers without giving them personal information.

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Date Night Challenge from 123Underwear.com: Week 1

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Jessica Downey

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

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No, that is not me posing

So the Date Night Challenge from 123Underwear.com is officially underway. Ever since my order arrived last week I have been extremely excited to actually wear what I chose. Yes, they sat in the box because I saved them for an actual date to wear them. After all, that is the point of the Date Night Challenge. Plus, I didn't want to let the newness wear off.

Technically the challenge was supposed to start with a coffee date this past Sunday but the date was rescheduled for last night. And it actually turned into drinks which seems more like a nighttime sort of thing anyway. Plus given all the other events of my weekend I didn't mind having an extra day.

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It's time to talk about (my) underwear

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Jessica Downey

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

Young woman putting on tight dress

If you've ever been underwear shopping with me you know that I am kind of picky when it comes to underwear. And when I say picky I don't mean that I have to buy the most expensive things or a specific name brand, I just mean that I tend to only like certain kinds. I definitely try to have some sexy things but I also like to be comfortable. 

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Tips when unfastening a bra

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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.

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

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Jessica Downey

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

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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?

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It's called having sexual confidence

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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?

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You're happy, so why cheat?

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Jessica Downey

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

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Cheating happens. Not that I am trying to say that I condone it or excuse it but the fact of the matter is that is happens. One thing that I really don't understand about cheating is why people do it. Actually, correction I do not understand why people do it and then go on and on about how much they love their significant other (and how happy the person makes them).

First things first, let's clear up the things that I understand.

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When the ex comes back around, part 3

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Jessica Downey

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

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I last left off (once again) with my story about Mr. BST. This time I left in the midst of our text conversation where he had asked how I would feel if he came to Chicago to see me and things were physical. And by physical I mean sex or at least a whole lot of sexually related things.

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We are human beings, not porn stars

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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.

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There is an exception to everything

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Jessica Downey

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

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I have always been the woman that can totally separate sex from feelings. I understand that people you are having sex with don't always care about you and that you don't always have sex with people you care about. Let's all be honest here, no matter how bad it might sound, sometimes people are just there for simple pleasure. It might be wonderfully blissful mind blowing pleasure, but never the less, it's just pleasure. I also understand that sometimes the line between sex and feelings can get a little blurry which is something that has caused me a little trouble in the past.

There was once a guy that I had this insane crush on but it became evident to me that the feeling was not mutual so I pretty much closed the door on the idea of dating him. As we spent more time together, we managed to become awesome friends. Until one night we engaged in a pretty heavy make out session that turned into two years of fooling around during which I took his virginity.

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An update on my quest for a summer fling

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Jessica Downey

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

Frustrated woman

A little over a week ago I wrote a post about how I was contemplating a summer fling. It was pretty much a unanimous vote amongst my readers and followers on Twitter so I decided that I should do it. Since everyone has been asking for updates I thought I would give everyone a few little details on what's been happening.

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

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Jessica Downey

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

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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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To fling or not to fling (with a 20-year-old)

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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 Sleeping in Bed

I've bitched mentioned before that I seem to attract a lot of 20 to 22-year-olds on OkCupid. If you read my blog, you know that I've encountered my share of younger men during my time as a single woman and it's definitely never been a secret that I am not a huge fan.

Honestly, I would like to say that I have some grand explanation for it but the truth is that things between me and the younger fellas just don't tend to work all that well. Nevertheless, I can't deny that some of these younger dudes are super hot which makes flirting with them a whole lot of fun (that is up until the point when they start annoying the crap out of me). And I should also confess that I find myself salivating far more than any grown woman should ever admit, over many guys this age during my commute to and from work each day on the bus (if you follow me on Twitter, you have seen my highly inappropriate tweets on this subject).

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New weekly feature: The single lady blogger is shaking things up

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Jessica Downey

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

Young Couple Speed Dating

You might have noticed that I didn't post any date ideas yesterday. And no, I did not forget about them nor am I a slacker. I have just decided to shake things up a little with a whole new weekly feature.

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Guest post: The one night stand

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Jessica Downey

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

The past couple of weeks I have had some of my favorite male bloggers talk about dating rules. Well this week Matt is throwing a different spin into the mix with some talk about the one night stand. Matt is the editor of LoveintheDumps.com, a dating/relationship comedy collective, and the upcoming Impersonals, a dating site parody.

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

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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?

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Survey Says: One in ten people wouldn't mind a text during sex

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Jessica Downey

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

Couple Taking Bath Together
Technology is a pretty big thing lately. As an avid Blackberry user and fan, I will admit that I love that I have access to everything anytime I want. I also have to add that I am pretty good with keeping it balanced - I put it away on dates and limit its use when I am with family. Which is why I was really surprised when a friend sent me an article about how one in ten people (under the ripe old age old 25) would not mind being interrupted by a text message during sex.
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Using a crutch for sex is probably not your best laid plan

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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.

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Please meet me in person before inviting me into your bed

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Jessica Downey

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

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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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Jessica Downey

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

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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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Let's be exclusive friends

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Jessica Downey

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

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

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Jessica Downey

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

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

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Jessica Downey

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

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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.

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

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Jessica Downey

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

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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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Man gets penis stuck in steel pipe

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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?

Deal breakers in dating: The bad first move

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Jessica Downey

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

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When you are dating guys over say the age of 25, it is inevitable that they have been on a date or two. Which also makes it pretty inevitable that they have kissed a girl and probably done all that sexual stuff too. Now, I am sure there is a 29-year-old out there somewhere that hasn't really been on a date with a woman. However, most of them have been around the block one or twice (some of them more times then they care to admit).

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

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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

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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):

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Anya Marina makes T.I. song hilariously sexy

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Jessica Downey

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

If you've heard the song "Whatever You Like" by T.I. then you definitely need to check out this version by Anya Marina.I have to say, I find this version to be even better then the original. However, I should add that just hearing the song doesn't do it justice. You have to also take a look at the video, which I nicely found on YouTube and have provided for your entertainment. It is a little bit of humor and sexy all wrapped up into one, which equals just plain awesome. I definitely give it two thumbs up. (If you haven't heard the original, check it out here.)

 

 

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A terrible advance won't get you into anyone's pants

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Jessica Downey

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

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Last night, I had a phone conversation with a man that I had been chatting with on OKCupid. I have to say that I was slightly amused by the conversation, though I don't think it was the kind of amusement that most people are looking for to make a good first impression. Coincidentally, this is why I recommend a phone conversation or two before you actually meet in person. 

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Introducing the Name That Penis Contest

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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.

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Signal for sex on the first date

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Jessica Downey

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

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Generally, I feel that you should go with the flow and do what feels right when on a date. Though, as a woman, sometimes I feel that there is a fine line between whats fun and what is just way too slutty. Which means there are things that maybe you shouldn't do on a first date. Back up for a second, there might be certain things you shouldn't do on a first date if you want a second date.

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