How do I get him into bed, or at least my mouth?
November 7, 2010 6:54 PM   Subscribe

How do I turn my friend into my lover? He is a bit younger than me, I am recently out of a relationship, and I am not sure he is in to me. I never do well with friendships with men, and we are so close, so I have no idea if I even should try. But I really want to.

Here's the background: he is 21, and I am 25. We have been coworkers for a while now. We hang out regularly, we are regularly mistaken for dating at work (where I could get in trouble for inter-retail-store relationships!) and we joke about that all the time. He told me I am funnier than Tina Fey! Who does that? But then when I have made jokes about actually dating (ie: "if they transfer me because they think we are dating, we will actually have to go on a date") he freaks out. Also: he might be a virgin? I am unclear. I want to hook up, but I can't decide if he will turn me down flat, and I would be devastated to lose the friendship. Men of the world, what is the best way for a woman to ask if you want to be friends with sexy benefits? Would you stop talking to someone who was into you if you weren't into them? Is it silly to think he would go for someone older? What are the signs that someone is secretly into you/ secretly praying you never solicit them?
posted by jenlovesponies to Human Relations (34 answers total) 3 users marked this as a favorite

 
>recently out of a relationship
Just make sure it's not a rebound thing, and that he knows it too.
posted by Neekee at 6:58 PM on November 7, 2010


But then when I have made jokes about actually dating (ie: "if they transfer me because they think we are dating, we will actually have to go on a date") he freaks out.

Freaks out, like, honest to goodness to freaking out? Not worth the drama. Sounds like he's a very nice work(!) friend to have.
posted by ThePinkSuperhero at 7:01 PM on November 7, 2010


But then when I have made jokes about actually dating....he freaks out

What exactly do you mean by "freaks out"? The question is asked because how he freaked out may indicate the scope of things. If he's freaked out over actually dating, that's one thing while if he's freaked out 'cause he's shy and inexperienced, that may be another.

If you're looking for signs, at some point when there's a break before seeing him for a while, put your hand on his arm, look him in the eye and say "Eventually, maybe not tonight, but at some point, you should come home with me. Think about it and let me know." He may still freak out if he's the sort he freaks out, but if you back off and give him time, he might get past the freak out stage and come around.

But really, like everyone else, you gotta go for what you want. You may not get it, but you can at least say you tried and move on.
posted by nomadicink at 7:04 PM on November 7, 2010


Response by poster: I might have exaggerated on "freaked out". But when I was joking with him, in the middle of the nine hours we hung out after work, he kind of frowned and said "Why would we do that?" And then recently we were going to a bar that we were concerned my boss would be at that night, and I said we would be fine being caught out together as long as he resisted the urge to make out with me, and he just kind of scoffed. Then we hung out for eight hours and walked arm-in-arm in the cold. That's weird, right? There is a reason I am banging my head against the wall.
posted by jenlovesponies at 7:14 PM on November 7, 2010


He could possibly think you're making fun of him, particularly if he finds outrageously attractive. Of course, if he's a naive, wild-about-you virgin and you just want to mess around, that could be the same thing.
posted by ThePinkSuperhero at 7:17 PM on November 7, 2010


He could possibly be gay and closeted. I suggest this only because of the "walked arm in arm" bit.

Really, there's not a whole lot of advice we can give, is there?

You either ask him out or don't ask him out. He either says yes or no. The risk that either answer would immediately blow up the friendship seems slight to me, but of course it's present. What if you ask him out and he's straight just not attracted to you? Would you be able to still be friends with him?

I dunno. I am kind of a coward, so even though I've definitely flirted in the past I've pretty much never been the one to ask someone else out. Well, I did that once but it turned out to actually be a butch lesbian, so while that was mortifying it didn't really cut the same way rejection would.

Anyway.

Good luck! FWIW, I say ask him out on a really for real date. The reward seems worth the risk.
posted by kavasa at 7:22 PM on November 7, 2010 [4 favorites]


21-year-old virgins are not known for their emotional intelligence and ability to communicate. Chances are, unless he's gay he wants a "real" relationship with you.

Best thing to do is to rent a movie at your place. Get a bottle of wine. Drink wine. Snuggle. See what happens next.

If he's gay, he'll probably let you know (and it might be a relief for him to have the opportunity to tell you, which might cancel out any awkwardness later). If he's straight, then a couple of glasses of red wine should do the trick.

Personally, I do not think 21-year-old straight male virgins have any business being platonic friends with single members of the opposite sex.
posted by KokuRyu at 7:45 PM on November 7, 2010 [7 favorites]


Open mouth, speak words. The fastest way to resolve "what does it meeeeeean?" is to, you know, ask and tell.

Because here's the deal: you can lay all your shit out for him, tell him how you feel and what you think, and one of two things will happen: he will respond positively, or he will respond negatively. Which way he goes will have basically nothing to do with you speaking your mind, unless you are obviously disrespectful about it.

In short: Ask. He will either say yes or no. He's going to either think yes or no anyway, so there's no harm in asking except you might get rejected, but it can't possibly be worse than being in the dark.
posted by Lyn Never at 7:45 PM on November 7, 2010 [8 favorites]


As pointed out by previous commenters, you won't know unless you ask. If a nice woman with whom I was friendly did as KokuRyu suggested for me, that would be awesome (mainly because I'm a big chicken when it comes to this sort of thing).

I would like to sound one cautionary note: Be wary of workplace romance. Be very wary of it. It has burned me personally in the past. My most recent ex and I met at work. For the (eight days shy of a) year that we were together, it was friggin' awesome: we could go out to lunch together all the time, *accidentally* meet up in the copy room to say hi, carpool together after sleeping over, email each other during the day, buy each other junk food from the vending machines, etc. Work was awesome, until that individual broke my heart. Now, life at work sucks because I have to see that individual on a regular basis (although, thank God/Buddha/FSM/etc. we're not in the same department), and every time I see that individual, it hurts.

TL:DR -> If you want to, by all means go for it, but have a backup plan in case you two hook up and then break up later on while still working together.
posted by AMSBoethius at 8:03 PM on November 7, 2010 [3 favorites]


Open mouth, speak words. The fastest way to resolve "what does it meeeeeean?" is to, you know, ask and tell.

Exactly. Use Your Words.
Like "Hey, would you like to go out on a date on Saturday?"
Everything else is a ham-fisted waste of everyones time.

(and please don't say "Eventually, maybe not tonight, but at some point, you should come home with me. Think about it and let me know.", because it sounds creepy, and if the guys not interested he may feel threatened/take a walk to HR)
posted by blueberry at 8:04 PM on November 7, 2010 [1 favorite]


Two personal anecdotes (I'm a guy):

Once in college a female friend of mine more or less told me, "I have a major crush on you." I don't remember how exactly I turned her down, but it was something like "I only want to be friends." I was very inexperienced at the time and it may have freaked me out a little, but also, I just wasn't attracted to her in that way. Things were slightly awkward for a little while after that... but we both got over it. She was -- and still is -- one of my very best friends.

In my mid-twenties, I was friends with this girl who was in a serious relationship. Some time after it ended, I realized I had a crush on her. A handful of months after that, because we already hung out it date-ey situations and I didn't feel comfortable just trying to make a move, I asked her on a date, using the word "date." She turned me down. I had been kind of crazy about her, but after that, I got over it surprisingly quickly -- I had needed to get that out there and find out. We are still good friends.

If this kid is inexperienced and shy and nervous (like I would have been in his place), KokuRyu's suggestion strikes me as not ideal. It can take people a while to learn signals that are, in hindsight, obvious, even painfully obvious.

I wouldn't try to read the tea leaves and figure out if the signs point to "yes" or "no" in this guy's case. As you've observed, it could go either way. Just ask him. Be extremely clear and straightforward about what you want: "I want to remain friends no matter what your answer to this question, but I am attracted to you and want you as my lover in a friends-with-benefits situation [that will or will not be exclusive, defining whatever other boundaries apply]."
posted by J. Wilson at 8:11 PM on November 7, 2010 [2 favorites]


I think you have very little control over whether he becomes your lover or not. Your best bet is to find ways to press your bodies together in the dark. Like KokuRyn said, get him drunk and snuggle. If he's into you, and you're spending all this time together, and he's not gay, and he's 21 like you say, he has a boner pretty much all the time and it's got your name on it.

You should push forward and find out. If he rejects you, it really won't be that bad, and I think you'll remain friends. Whatever the case, finding out the truth is better than the uncertainty. Good luck to you!
posted by boghead at 8:17 PM on November 7, 2010 [1 favorite]


Also, if I were secretly praying that you not solicit me, I don't think I would walk arm-in-arm with you. So, he could be secretly hoping that you do express interest. He could just as easily have never considered the idea.
posted by J. Wilson at 8:17 PM on November 7, 2010


The reason I don't like boghead's suggestion -- just press your body against him and check if he's got wood -- is that you want to remain friends with him. That's much more invasive than just telling him how you feel and what you want, and if he's shy and inexperienced and not into it, that's more likely to make him feel uncomfortable. (Even if he is into it, that might be too much for him when it's out of the blue. Or it might not and he might love that.) Friends don't make friends feel like they're trying to take advantage of them. But friends do ask friends on dates and respect each others feelings.
posted by J. Wilson at 8:22 PM on November 7, 2010 [6 favorites]


He is into you. He is shy. He is scared.

Get him drunk and kiss him. No talk, just a big ol' smooch. Go for it.
posted by LarryC at 8:51 PM on November 7, 2010 [1 favorite]


at work (where I could get in trouble for inter-retail-store relationships!)

This screams "Bad Idea!" very loudly, especially in the context of the recent breakup, the possible virginity, etc.

But people violate those "no dating" rules all the time, so I understand if you want to go ahead anyway. Like everyone keeps saying, though, you'll have to cowgirl up and use real words (as compared to indirectly hinting in ways that are open to sixteen kinds of misinterpretation). Yes, you will risk an embarrassing rejection, but it's the only way you are going to get clarity on this.

And while I'm in no way suggesting getting him too drunk to think straight, these kinds of things are always easier after a glass or two of wine. Stop with the weird hinting, grab a few drinks, and make a move.

(But I still think that this is a Bad Idea.)
posted by Forktine at 9:07 PM on November 7, 2010 [1 favorite]


You know, I kind of wonder how Shakespeare would handle the "inter-retail-store relationships". You only live once.
posted by KokuRyu at 9:11 PM on November 7, 2010


I'd be wary of the "get him drunk" suggestions. People do things they regret when they're drunk. He might go for it, you guys sleep together. The next day, you're super excited because he 'totally likes you' and he's super freaked out because he made a mistake, and now he has to tell you it was a mistake. This is the only way I can see your friendship being compromised. Just plain talking to him shouldn't do that.
You're best going along with everyone who suggests using your words. An open, clear line of communication is key when trying to understand someone and their feelings.
posted by shesaysgo at 9:14 PM on November 7, 2010 [4 favorites]


I don't like the "get him drunk" angle. Talk to him instead.

(How many responses would be "get her drunk" if the declared genders were reversed? Not many, I'd wager.)
posted by Sternmeyer at 9:20 PM on November 7, 2010 [17 favorites]


fwiw I also think the flippant responses could well just be defensive chatter, aimed to not make you think he is trying to get into your pants/ protecting himself from possible rejection.

I could have seen myself doing something equally boneheaded around his age if a female friend I cared about made similar comments.
posted by edgeways at 9:26 PM on November 7, 2010 [1 favorite]


"Why would we do that?" And then recently we were going to a bar that we were concerned my boss would be at that night, and I said we would be fine being caught out together as long as he resisted the urge to make out with me, and he just kind of scoffed. Then we hung out for eight hours and walked arm-in-arm in the cold. That's weird, right?

Yes, that is weird. For me, that would be an instant turnoff. I mean, do you really want to make out with someone who scoffs at the idea of making out with you? Best case, he thinks you're already ON a date and that it's obvious he can't stop fantasizing about you, so he is trying to cover it all up like edgeways suggests. But yeah, being old, I'd have no patience for trying to date someone who couldn't help take the flirting to the next level. He's 21, not 16. I'd assume he either didn't like me, or he had some problem expressing it when he has warm feelings for someone, which does not make for a good relationship in my book.

Anyway, good luck asking him out. I hope you go out and that he proves my harsh assessment totally wrong. At your wedding shower you can talk about how you'd have missed out entirely if you'd listened to the Internet. But until then, if he says yes, I'd watch for other signs that his style is to hold back and express derision when you ask for closeness. And if he says no, I wouldn't worry too much, as he apparently isn't too cautious about the signals he sends others.

Tl;dr-- Tell him to get off my lawn.
posted by salvia at 9:54 PM on November 7, 2010 [2 favorites]


I might have exaggerated on "freaked out". But when I was joking with him, in the middle of the nine hours we hung out after work, he kind of frowned and said "Why would we do that?" And then recently we were going to a bar that we were concerned my boss would be at that night, and I said we would be fine being caught out together as long as he resisted the urge to make out with me, and he just kind of scoffed. Then we hung out for eight hours and walked arm-in-arm in the cold. That's weird, right? There is a reason I am banging my head against the wall.

Yup, weird. But I can't conjure a scene where a hetero guy says, "Why would we do that?" when offered a hypothetical make-out with a chick he wanted to make out with.

By all means, go for it; I've been wrong more times than you (judging from your age); but my bet is that you're in the dreaded "just-friends" zone.
posted by IAmBroom at 10:18 PM on November 7, 2010 [1 favorite]


Advice I once got from my father: when you're walking somewhere together, nonchalantly hold his hand.
posted by lover at 10:40 PM on November 7, 2010


get him drunk

How about not drugging someone for the purposes of sex. Especially someone you work with.

Have you considered he's "freaking out" because he's not interested and is feeling harassed?
posted by rodgerd at 11:21 PM on November 7, 2010 [2 favorites]


'he kind of frowned and said "Why would we do that?"'

'as long as he resisted the urge to make out with me, and he just kind of scoffed.'

As long as you are only dropping hints and not directly asking him out, his only choice is to respond with equal and opposite hints that he's not interested. It's clear to me that he is not interested, from what you write here.

In my experience, the next step is for you to escalate your hint-dropping, ramp up the emotional blackmail, and eventually explode in a publicly embarrassing mess in which you accuse him of cruelly leading you on by being unclear about his intentions. The bonus is that he will be reluctant to approach HR because of your personal friendship, so as long as you embed intermittent complaints and hints into the overall context of that friendship, you will be able to go on harassing him for years with absolute impunity!

Harassment is an ugly word, and obviously the furthest thing from your mind, but this is what your situation is going to turn into if you carry on as you are.

Seriously, either ask him out or clam up. Nthing the recommendations against using intoxicants to take advantage of him.
posted by tel3path at 11:57 PM on November 7, 2010 [2 favorites]


A couple of big glasses of wine should do the trick.
posted by KokuRyu at 12:06 AM on November 8, 2010


At that age I could have easily taken your 'hints' as teasing.

If you really want to date this dude, make him undeniably aware of you affection without hedging for rejection.
posted by HFSH at 2:47 AM on November 8, 2010 [2 favorites]


Please do not assume that because he's 21 and responding negatively to hints, that he can't communicate clearly or doesn't know what he wants. If he's as inexperienced as the OP assumes, it may not be because he has poor judgement or is deficient in some way, but rather that he's very clear about where he does and does not want to stick his body parts. Using alcohol to disinhibit him into doing what he must 'really' want because he's a GUY! and we all know what GUYS want!! unless they're GAY!!! may not be something he'd thank the OP for.

It doesn't look to me like he's misunderstanding the OP, it looks like the OP can dish out hints but can't take them, and may be deliberately choosing (cheered on by the hivemind) to avoid having to hear 'no', and to arrange for 100% of the risk to land on the guy.

The delicate dance of ambiguity is great when friendship and employment are not at risk. In this case, both are at risk AND NOT JUST FOR THE OP. If I'm wrong, and the guy is burning with desire for the OP but is unwilling to express or act on it, this is best discovered by the use of an unambiguous yes or no question.
posted by tel3path at 3:10 AM on November 8, 2010 [6 favorites]


I am recently out of a relationship,

How recently? Did he know about it? Did you hang out with him during the relationship? Did you talk about it? Need more information here.
posted by Obscure Reference at 4:33 AM on November 8, 2010


But I can't conjure a scene where a hetero guy says, "Why would we do that?" when offered a hypothetical make-out with a chick he wanted to make out with.

Really? I don't think it take that much imagination to conjure. If Guy is shy, young, and a virgin, and he's very much into Girl, who is older and, for all he knows, completely joking and not at all into him like that, then that reaction is perfectly plausible.

On the other hand, he might be perfectly aware that it's flirty teasing, and this is his way of saying no without saying no, since he hasn't been asked a yes/no question yet.

With this guy, it's clear that this game that's being played isn't going to get results. OP: time to piss or get off the pot. Otherwise you're making yourself uncomfortable and you're likely making him uncomfortable, and with absolutely no purpose.
posted by J. Wilson at 5:08 AM on November 8, 2010 [1 favorite]


If you are hanging out for eight hours at a time, that's enough time to say, "I think we should have sex. Just for fun. No pressure if you aren't into it. You want to?"

Seriously, go for it. If he's gay, well, 21 is pretty normal age to come out. If he's a virgin, this might freak him out, and he might act a little weird, but give him a chance to wrap his mind around it.
posted by Leta at 6:37 AM on November 8, 2010


Honestly, he doesn't sound interested to me (gay is also possible) sexually at all from what you say. But whether or not he was, if you're going to get in trouble for dating at work, wait until one of you quits to ask him. (It's retail. Both of you will not be still working there 15 years later.) That way, nobody gets in trouble, and if things go horribly badly you don't have to see him afterwards. Win-win!
posted by jenfullmoon at 7:23 AM on November 8, 2010


"Do you want to go on an actual date with me to/ on ______"

If he accepts, during the date you can say

"Do you need a ride back to my place?"
posted by WeekendJen at 8:30 AM on November 8, 2010


Response by poster: Problem solved, guys, and here is what happened:

I was getting a lot of mixed signals. For the record, we are really outside-of-work friends to the point where we were hanging out all the time and text messaging all the time, and we had a nice solid friendship to work from. I decided to ask him if he wanted to go out on NYE, because that is the one day a year you can kiss someone and have it not mean anything if they don't want it to. He kind of went back and forth on NYE, because he hates crowds, and I wanted to do a bar thing, and he only decided not ten minutes after I brought up a recent surprise set-up with a stranger. If that wasn't a signal, I didn't know what was. Then he went out and bought a shirt so we would color-coordinate. I could not possibly take that any other way. Then I kissed him at midnight, and he kissed me back with gusto, and we danced and stayed out all night, and then when I dropped him off he exited without a kiss. Now, had I had access to Metafilter that night I might have posted on here from the bar bathroom, because we were talking about how we really don't have a huge age gap, and what our friends think, and all that (he also mentioned that he was a virgin). It was very exciting to be right! I had to see him at work right after that, and we both referenced that we were most certainly not drunk (and I would like to point out that we have never ever been drunk in front of each other, though we have had drinks we never even made it to tipsy) and that he might have given me his cold. We went to a movie the next night (my idea, he paid, he complimented my outfit, but we didn't hold hands) and then we went out last night.

Now, we have been slowly introducing each other to our friends in a way that, to me and to everyone else, I think, indicated romantic interest. I invited him to a bar party, where we danced, drank (again, not much) and he met a bunch of my friends, even though he hates crowds and strangers. I thought I was getting signals- and can you blame me?- so I kissed him- twice- and he kissed me back- twice- so I confessed that I was really into him, and had been for a while. He said he was not interested in me, and we left the party and I kept asking him why the hell he had kissed me back if he was interested, and he said he was sorry, so very sorry, and that he liked someone else. I pointed out that as we are talking, working together, or hanging out daily, I know of his entire social circle and I would know who this person is, and then we didn't talk on the ride back to my place. And then I just kept asking him why he hadn't just pushed me away, why he kept giving me signals, why he couldn't just TELL me he wasn't into me when I was being fairly obvious.

And then he told me he wasn't sure if he was "straight or gay or bi" and so he didn't date. He also told me I was the first person on earth to hear this confession.

I stopped being mad and started hugging him, and we talked about this- I talked, he kept his head buried in his hands and wouldn't let me turn on the car light lest I look him in the eyes. I feel terrible for him, though he feels more terrible that I could imagine. At one point he said he rather I had stomped off at the bar and gotten a ride from someone else, because then I might have just slashed his tires at work, and he wouldn't have turned me in, because then at least we didn't have to talk about his confusion (for the record, I have never and would never slash tires). He said he would have given up our friendship rather than discuss the issue. He said he wished he had never insisted I accept his friend request despite my prior "no coworkers" facebook policy. He also said that he didn't realize I liked him till around NYE, and he realized he was giving me confused signals because he himself was confused. He admitted that perhaps we were dating without dating, and going on things that I really couldn't help but assume were dates. He also said he made up the other person he was interested in.

The beauty of retail is that we had to go straight to work at that point, basically. And now, sleep deprived, I am writing this after a full and awkward work day. We were a little stilted conversationally, I would say, because of the giant pink elephant in the room, but otherwise pretty normal, so I think we should be fine as coworkers. But as for our friendship, I am not going to ask him to hang out unless he wants to, and I think I am going to leave the topic alone for at least a few weeks- he should figure himself out, I think, and he should talk to someone about it, maybe a professional, but I am not going to push him or anything.

TL, DR: He is a (probably) gay (definite) virgin, this revelation is probably not going to cause any problems at work, and we are probably going to continue to be friends. Hopefully. And I did not drug him.
posted by jenlovesponies at 12:07 PM on January 9, 2011 [1 favorite]


« Older DIY solution to stay warm this winter and watch TV   |   Looking for a specific ring for my sister. Mine. Newer »
This thread is closed to new comments.