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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