Hello Captain Awkward,
I think I may have flirted a bit too much with this boy. He’s eighteen; I’m twenty-six. I have a boyfriend, and he knows this; I’m very happy with my boyfriend, and he knows this. Still, he is cute and awkward and rather nice, and when I look at him, I think to myself “Gosh, some girl who is a bit younger than me is going to be lucky to have that boy someday.” It so happens that women are scarce around here, and I would rather he blossomed from awkward to charming than from awkward to bitter. So I flirt with him.
I see him a couple of times a week as part of a singing group, and a couple of weeks back, as we were saying goodbye, he mentioned that he looks forward to rehearsals because he gets to talk to charming women, which I completed with the commentary “… he says, looking charmingly at the floor.” I regretted that response a minute or so after saying it, because the way he’d talked about looking forward to rehearsals made me suddenly remember what it’s like to be eighteen and horny and prone to crushes. I wished I’d said “I hope you’re not wasting all your charming flirting on me” instead, or some similar remark that would have seemed less like I welcomed the crush that I later realized he might have been admitting to.
I’ve been less responsive to him during rehearsals since then — I still joke with him as much as with the rest of the group, but I’ve tried to cut off the flirting. Still, I wonder if what I really need to do is make an opportunity to speak with him and ask “Do we need to talk?” Perhaps it would be easier on him if he knew exactly what was happening, from my end. What do you think? Do I take him aside and tell him what I’ve told you — that I don’t want him for myself, but he’s cute and awkward and rather nice, and some girl who is a bit younger than me is going to be lucky to have him someday? Should I try to get that message across casually, rather than in a private discussion? Or is it better to just stay quiet and hope he’ll find his own way around the sudden lack of flirting?
Thanks.
– Overly Flirtatious
I wouldn’t worry too much about managing this guy’s feelings, Overly Flirtatious. We live in weird times. Never have we been more sexually liberated, but then, because you could actually follow through without having to sew a scarlet “A” to all of your clothing, there’s this weirdly fraught thing where you wonder, “I told him he had a nice smile, too. Am I expected to follow through?” Our grandparents had ballroom dancing, which allowed you to rub up against members of the opposite sex and talk and laugh and flirt and touch in a socially-sanctioned way. We stay at arm’s length, escalate to text messages, and then suddenly we’re in Fuckytown having skipped a whole bunch of steps along the way. Slow it down, people! Having small crushes on people who make you feel awesome when there’s no chance of them getting out of hand…Oh man, it’s the best. Crushes give you a reason to get up in the morning and wear pretty outfits and lipstick and smile and then go home and smooch your sweetie with an extra spring in your step and sparkle in your eye. If I close my eyes, I can count at least five twelve active crushes that I have going on right now. They’re not necessarily sexy-crushes, just, hey, you’re so attractive and smart, let me sit here looking at you and listening to you be brilliant for a while, okay? The day I have to give up crushes is the day I want to give up living.<br>
I would just keep talking to your friend in a friendly, engaging way and enjoying his company. Assume he can handle himself, and he will handle himself. If the weird flirting ever comes up, either because he pushes the issue or because he’s so goddamn adorable you can’t help yourself, you can just say “I like choir, too – I get to keep my flirting hand in with super-cool men like you. I hope I didn’t overstep the other night.” In other words, just acknowledge the awkwardness and the adorableness, banter like you’re in a Depression-era musical, and let him walk away feeling ten feet tall.<br>
Yeah, I’ll be watching Ginger Rogers clips all night, thanks to you. She was a major dame and never had a dumb moment in her life.
CaptainAwkward.com 
Solid advice, Captain! I second the thought that there is a whole lot of territory between “hello” and sex and, sometimes, it is fun to hang out there. Plus, play-flirting is fun to do at places, like, oh, shows at the Double Door, or while acting as wing-man. I know I’m going home alone, but maybe I get to go home with everyone feeling more awesome, witty, and pretty.
I am so glad you choose to do that. Thank you.
Excellent advice! The ability to have a strong crush without anything getting out of hand is one of the best, in my opinion. I’ve only got one crush at the moment, but let me tell you, it brings me such joy.
Somewhat after the fact…(hello! I was just alerted to the existence of this amazing advice site yesterday, and I’ve been reading back through the entries and sort of generally admiring the sensible, compassionate, and insightful answers offered therein), and, well, this entry made me really happy.
I’m single, comfortably so, with a not-disastrous-yet-not-productive dating history, and I have, right now, a fair crush on a really delightful coworker. He’s not single, our employment situation is pretty precarious, and our job prospects and lifestyles are unlikely to overlap after this situation.
I really like this coworker. We have chemistry. We make each other laugh in a way I have never experienced with another guy. I find him physically attractive (this is a rarity with me, which is part of why I am comfortably single). And yet, for all those things–attracted to him, feel a mutual vibe of like, real personal chemistry, genuinely enjoy seeing him and interacting with him–it doesn’t really bug me that he’s not available, and I don’t feel hung up on the knowledge that eventually, maybe not too far from now, we’ll both be in other jobs (uhh, hopefully) and not see each other.
I have been idly wondering why–as the idea of someday having a serious relationship with someone is not unattractive to me–I can feel all that sparkage around this guy, knowing there’s nothing to it beyond our current enjoyable workplace interactions, and yet not feel a pang that it isn’t gonna be. And this entry sort of made it make sense–duh! I can have the crush and having the crush can be fun, and that can be the end of it. Feeling the spark doesn’t mean that it has to catch fire to have been real.
And that’s fantastic.