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

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).

Long story short, while I try to really keep an open mind about most things in life, I am not sure how I feel about this whole dating a younger guy thing. Which is why I was a little thrown when one day, as I was staring at one of these young studs (all the while praying that he was legal), I couldn’t help fantasizing about what I would do if I had this man alone in my bed.

And so, the idea for a hot summer fling with a younger man, preferably one in his very early twenties, was born.

Now, keep in mind that this thought first came to me several weeks ago and I still haven’t found a way to make it happen. So what’s the problem here, really?

Well honestly, as much as I think a summer fling with a hot young thing is a phenomenal idea, I can’t help but be torn between the responsible adult that keeps saying “a 20-year-old, seriously Jessica?” and the fun free spirited woman in me who thinks it would make for one hell of a summer. 

My trepidation could also have something to do with the 24-year-old that I dated briefly last winter. He was a beyond adorable, fantastically sweet guy, who was also great fun to make out with. We had a blast together for a while, but it eventually ended in a really weird fashion that frankly rubbed me the wrong way (no pun intended). Essentially he freaked out when things started to get a little too hot and heavy while we were naked, which of course made everything extremely weird. The end result was that I was left wondering if it was something I did (or didn’t do) that made him want to stop all the naked fun. Let’s be honest here, who wants a summer fling that is going to freak out when the fun starts? I mean, isn’t fun the whole point of a summer fling?.

And then of course, we have a recent post by Skye Blue over on which leads me to believe that I am not the only who is left feeling frustrated and disappointed by younger guys.

Don’t get me wrong here, I am not saying men my age and older are saints by any means. And I am definitely not saying that dating them is all rainbows and butterflies. In fact, a good portion of my dating stories are about my misadventures with older guys. But, what I am saying is that I tend to have an easier time with older men. There is something about the way I relate to them (and them to me) that just seems to click nicely – and that’s really how it’s always been. Let’s face it; a 22-year-old is probably really not at the same stage of life as I am anyway.

But then there is still the chance that this could be a really good thing. Twenty-somethings are young, reckless, and a whole lot of fun (especially the horizontal kind). And maybe that is something I need, especially since I am approaching a fairly big birthday this fall. I mean, I’d be lying if I said the idea of spending a few nights a week naked with a guy that’s 10 years younger than me doesn’t intrigue me, especially if he makes breakfast for me in the morning. Wait, a second, do 20-year-olds even do that?

And as I am having all these thoughts the messages keep rolling in.

The conflict in my head rages on. I think there’s a part of me that’s hoping that now that I’m putting this out there on my blog that at least one of you will say “go for it Jess” or that I may even get offer or two, so the decision will be mad for me (well kind of anyway).

So, what do you think readers? Should I get my summer fling on with a hot piece of ass 20-something?

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

  1. You have seriously taken the words right out of my mouth, Jess. What a terrific post.P.S. My vote was entirely no until you mentioned it was a hot piece of ass put it so eloquently.Go have some summer fun. And report back. In detail!xxooLG

  2. oops. it didn’t let me strikethrough the “mentioned it was a hot piece of ass” part. I guess that html is not permitted. thanks interweb. now i look like a ruh-TARD.anyway – that’s what it was supposed to look like.doesn’t change my opinion at all, though :-p

  3. Thank you so much! I thought that was a fairly nice touch. And thanks for the encouragement. Though that sounds really weird, shouldn’t encouragement be for something like saving the planet?? :) Summer is all about fun. I will definitely report back.

  4. From one Jess to another… I don’t know how old you are but is there even any question?! Ok, my ONLY reservation for you is that a 20 year old cannot get into a bar and, in my experiences, bars play a critical role in the pursuit of a fling. Otherwise, hell ya girl, go for it. As long as no one’s feelings get hurt –it’s all good. And by the way, I’ve had the same experience on OKC –lots of younger guys. But I think it’s great! Nice that the old days of old men dating younger and younger are being turned on their head. Also, I’ve learned that young guys keep YOU feeling young. They’ve got the energy, enthusiasm and optimism that we may have lost (a bit). And that’s not even addressing the fact that the older woman-younger man combo is a perfect match for sexual energy. Again, there’s little here to question. Have fun!!

  5. get em! if there were any 20 year old women (or women of any age) trying to boogie w/ me you better believe i wouldn’t have time to blog about it.

  6. Nice to know I am not the only one with the younger guy thing on OkCupid! And you are so right, they do make you feel young. That is true about the age and I would definitely be ok with a 21-year-old. Though I will admit that part of the turn on of the 20-year-old is the fact that he can’t get into bars. :)

  7. That is to find each of us a summer fling. Not one to share – though that would be awesome blogging fodder. :)

  8. I say 100% go for it…as I’m planning to…though I’m thinking you may want to up the age just a smidge…say to 21…I mean…what if he came over and you gave him a beer…you’d literally be serving someone underage…lol…*points to self* rule folllower!…that being said…with that logic technically I could actually move my age floor down to 19 (since I’m in Canada afterall…Go Canada GO!)…I expect updates on the escapades!!

    PS…did you ever find out why the 24 year old freaked out? was he a virgin maybe?

  9. It’s funny you should mention upping the age to 21, I was just thinking about that the other day. So, yeah, I am flexible about that. :)

    As for the 24-year-old. No, I never found out why he freaked out. It was the strangest thing. Sometimes I think I should have asked, but I kind of feel like if he really wanted to tell me, he would have. You know?

  10. Go for it! So if I, as a 22 year old, were going to have a fling, would I do it with an older guy?! And no, guys my age DO not make breakfast. And are generally inconsiderate.

  11. I say fling with whatever age you like. I thought younger because I usually date guys that are older and all these younger guys seem to keep hitting on me, so why not :). That is quite sad about breakfast I was really hoping for that.

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