5 Things I Wish I Had Done While I Was Still Single

I’m really into my boyfriend — I wouldn’t trade him for any other boyfriend or series of men. But you don’t usually know when you’re going to meet your “special one,” (to borrow from George Saunders’s short story “Victory Lap”), so unless you’re in an open relationship (I’m not) everything that happens beforehand is all you get. I’ve also dated my fair share of dudes, so I’m not suggesting I catch up for years of lost time here, or even participate in an entire pre-boyfriend do-over. I’m just saying, if I had the chance to go back in time and tweak a few things here and there, this is what I would do.

I would have a threesome. Having a threesome always kind of freaked me out. The implicit advanced sexuality of willing threesome participants, the fear of not being proficient or coordinated enough to juggle a third body and all its parts… whenever it came up — during a special moment with a dude, in conversation at a party, wherever — I’d make all kinds of excuses: “Intimacy is really a one on one thing”; “Sex is about the connection between you another person, where does a third entity fit in?” Wouldn’t the additional person feel like a third wheel? What if I was the third wheel?

In retrospect, my fears seem kind of petty and childish, and I wish I had gotten over them in time to just see for myself. “You don’t know until you try it” — there’s a reason expressions like this are clichés. And what’s the worst that could have happened anyway? I would have had the chance to score with two people simultaneously, and… sorry, what turn could this question possibly take that would end in anything less than a sweet ass time?

But for argument’s sake, let’s say having a threesome did turn out to legitimize all, or even just some, of my worst fears, I’d only have to have my first threesome once. It’s not like buying a ten-pack of yoga classes where you commit to all ten classes when you sign up (and no transfers!); there are free trials. And if it turned out not to be my thing, I could have been done with it, end of story.

I would have a sexual encounter with a woman. I’m not talking about a token lesbian experience, like, for street cred or anything. And I’ve made out with girls before — for fun, with friends, as a teen exploring my sexuality. But, I’ve never been intimate with a woman despite all the many times I’ve fantasized about it, in the way that you might be primarily attracted to one sex, but that doesn’t mean it’s the only sex you’re attracted to, ever.

Something about knowing your own body and what you like, and then interacting with another person with the same kind of body and possibly the same kind of likes, (or different ones), interested me. I imagined women with other women to be communicative about their needs and intuitive about their partner’s; to take their time and ask a lot of questions, such as, what does my companion like, and what does she want? Of course, had I the chance to see for myself, I wouldn’t have to make broad, sweeping assumptions about what women are like with other women in intimate situations, because I would know.

I would learn to break up with a dude I didn’t like. This is going to sound really pathetic and it’s embarrassing to admit, but I’ve always liked dating boys so much that sometimes dating them had less to do with the particular them than it did the someone, anyone. Boyfriends of the past, this does not apply to (most of) you. Any actual long and meaningful relationship I’ve had has been for real; I’m talking about those intermediate couple of dates, several sleepovers, few month flings. When starting to date someone, as long as they were “cool enough” and/or mildly funny and attractive, I would schedule an appointment to get my bikini line waxed pronto, and scour the Internet for cool shows and art openings so I would have things to invite them to. The will of wanting to have something going on was often so strong — I liked having news to report back to my girlfriends, it was fun to have someone to do stuff with, and of course to make out with — that it would override the whole “taking the time to decide whether I actually liked the person or not” step.

So, if I got to hit the redo button, I would set one mandatory rule for myself: be honest. Like, if a guy was kind of weird and douchey, or if it was obvious from the get-go that he did not have my best interest in mind, end immediately. Not to be discussed, considered, salvaged by a series of “second chances,” just donezo. I’d be able to book a second date with someone I had mild feelings for, or who was kind of interesting but I just wasn’t sure if I was “feeling it” or not; I just couldn’t entertain losers. Which granted, would make dating in Brooklyn kind of difficult — and as a result of instating a no-loser policy, my social calendar would drastically diminish — I would have to accept that. But the good news is, I would get to spend my newly acquired free time and energy doing all kinds of things, like: further pursue my writing career, learn how to drive a stick, ferment my own sauerkraut, revisit tap dancing lessons. Or watch Over the Edge for the seventy-ninth time and paint my toenails black before meeting an arrogant loser for a late night at Union Pool.

I would learn to not have emotional diarrhea of the mouth early in. Before professing my “feelings” to my casual dating partner in the form of familiar sayings like “I love you,” and “I’d like to marry you someday,” or even nonchalantly starting sentences with “When we move in together, let’s…” I would wait a bunch of months. Dudes smell this desperation permeating through your sweat glands from miles away as just what it is: fear motivating you to try and sink your dirty claws into their biceps and belt loops. (Again, in any given instance, whether said dude was right for me or not was probably at the bottom of my pros and cons list with more important variables like how he parted his hair or what songs he liked to sing at karaoke, at the top.) And, as dating folklore has pretty much always warned, the best way to push a potential mate away is to try and pull them closer. True that.

I would refrain from sending that last text message. You know those in-between texts dudes send where they want to know how your day is going, or they just remembered the name of the movie neither of you could think of three days before when you last hung out? Those were always nice to get. But because I’m so impatient, I would basically wait for the back and forths to end with a “Do you want to hang Tuesday night?” And if it didn’t come, guess what I would do, nine times out of ten? I would try to initiate a hangout myself! Even though I had the last time, even though I swore I would play it cool just once, even though I really could have used an early night’s sleep and a face mask. But I just couldn’t wait, knowing it would be another two more days until I might be asked to grab a drink or catch his friend’s band or see if the movie whose name he finally recalled was on Netflix Instant or not. Plus, maybe I’d go to Philly that weekend to visit Emily and then I surely wouldn’t be able to see him for another bunch of days, so we should probably get this squared away now. But wouldn’t it be cooler if I just didn’t send that last text? TC Mark


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  • Thomas

    Great article. So true, and I’m recently single, so it really resonates.

  • http://www.itmakesmestronger.com/2012/06/5-things-i-wish-i-had-done-while-i-was-still-single-2/ Only L<3Ve @ ItMakesMeStronger.com

    […] Thought Catalog » Love & Sex Add a comment […]

  • Isaac

    It’s never too late to have a threesome.

  • Ana

    you speaks true!

  • Stephen

    Statistically speaking, you’ll more than likely get another chance to do all of these… just saying.

    • Sara

      Agreed. You sound young – it’s bound to happen. Don’t limit yourself and set your own boundaries.

      Another thing, if you don’t do it now and you’ve been thinking about it (you even wrote an article about it) you will, at some point, resent or regret your current situation. It has to come out, at some point in your life. Ever heard of a mid-life crisis or those desperate housewives?

      Trust me, it’s part of growing up. Luck!

  • JAD

    not to be a dick, but this article has reaffirmed my deep disgust with 95% of girls. who are you to say someone is a loser? so if a guy doesn’t sing your favorite songs at kareoke, they don’t text you 10 times a day, and they aren’t “at least mildly attractive”… they’re losers? you’re saying by definition that they are losing at life? well if one thing is for certain, it’s true they’re losing out on you. and from my perspective, that makes them winners.

    • JLUA

      I wish we still had that “like” button.

      • http://www.facebook.com/careuhsellxo Angela Joyce

        woah woah, I love this article…but what happened to the like button?

    • Domino

      *karaoke. and if you’re digusted with 95% of girls… well then i guess you don’t get laid much huh buddy?

      • Mushion

        Maybe Jad is just very picky. I think it’s good to be picky rather than have sex with a bunch of people you didn’t like.

    • guest


      and yeah where the fuck did that “like” button go, thats some bs

    • Caitlin

      wait, because she’s a girl she can’t call someone a loser? maybe it’s just someone she doesn’t get along with. girls are allowed to be just as picky as guys are, and when it comes to “boyfriend” material it’s actually in everyone’s best interests. some other girl might care about other things and not the things she mentioned, and that’s okay too. your rant sounds like the ramblings of an insecure dbag who blames all girls for never getting your own girlfriend.

      but hey, at least your right hand will always love you.

  • guest

    ryan! you went back to being the worst on TC, too bad so sad :'(

    • guest

      holy fuck, this isnt ryan lol, oopziz

  • I know how you feel.

    Hello, did I write this? I think we might be the same person.

  • Galina

    Constantly referring to men as dudes is very grating, much like the rest of this clichéd article.

  • http://gravatar.com/blackpaperbird blackpaperbird

    popping your threesome / sexual-encounter-with-someone-of-the-opposite-sex cherry isn’t like buying a dress and then returning it afterward. if you don’t find it suits you, you can’t always get all your metaphorical money back (perhaps I’m more aware of buyer’s remorse because I don’t live in a country which has returns policies based on ‘changed my mind, here’s the receipt’).

    also, often that baggage you tried to get rid off but are stuck with affects someone other than you (your future partner); or, if you aren’t the one with baggage, you could have left someone else with it (the other party involved). much the same as one-night stands have the propensity to do.

    so perhaps you should be glad instead… for you could be writing a list of things you wish you hadn’t done before meeting your special person.

    • Renata

      So you consider having a threesome a baggage that you have to get rid of/something that could potentially affect a future partner?

      • Jebob

        Yes, RENATA. Seriously.

    • http://www.facebook.com/sandy.allison.18 Sandy Allison

      Sex-shaming much? Yeesh…

      And to the author: you don’t need to be single to have a threesome!

  • Svenry

    You shouldn’t have to be single to be allowed to have a sexual encounter with a woman.

  • http://travellinginternationally.wordpress.com travellinginternationally

    Reblogged this on Threesomes and variations and commented:
    Even though this blog is not entirely dedicated to threesomes, it is a very well written thought piece about threesomes and dating in general.

  • http://setoshino.wordpress.com Setoshino

    Reblogged this on The World Without Us.

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