Ask him out...but what if I can't?

September 16, 2010 8:32 AM

So I decided to ask him out...but what if I can't? (Another special snowflake, no doubt :-/)

So there's this colleague of mine (same general field, different organizations). I've recently started getting to know him a bit better and I've developed a major crush. I think I've finally gotten up the courage to ask him out, but maybe it's a bad idea. Sometimes I think he might be interested in me but sometimes I'm not so sure; he's pretty shy and quiet (as am I) and I can't really read him. Examples: he invited me to a party he was throwing that he didn't invite any other "work-related" people to, but then he more or less left me to chat with his other friends once I was there (a lot of the time he was setting up food, etc., so there was some reason to this, but why did he invite me if he was just going to neglect me?). We have lunch together one-on-one about once every two weeks - he initiated this but we mostly trade lunch invitations back and forth these days. This is fun but we range all over the spectrum between "great conversation" and "both staring down at our plates without anything to say", and even the best conversations we have are usually to do with our work rather than anything hugely personal.

Anyway. I know the best way to find out if he's interested is to just ask him. I managed to come up with a legitimate excuse to suggest that we go for a drink while hopefully not forcing the implication of anything other than friends in advance. I'm kind of hoping that once we both have a bit of alcohol inside of us my nerves will be calmed enough that I'll be able to take the conversation a bit beyond our normal how's-work-going and rant-about-the-boss type of conversations and hopefully express directly that I'm interested in him. Only, I have no idea how to actually accomplish this. I know I'm probably overthinking everything. But anyway, I guess my questions are:

1. Do you have any suggestions for how to steer the conversation a bit more into "I'm interested in you" territory? Obviously I'm not going to make a declaration of undying love or anything but since I will still see him in professional contexts regardless of the outcome I'd rather not make this a completely awkward conversation. Also it's been a long time since I've dated anyone so I'd rather not come across as completely desperate.

2. Is there something I'm missing here that makes this completely a bad idea? I'm terrified of doing this - the only other time in my life I ever asked someone out, he didn't answer at all and then avoided me for a month (this was more than ten years ago and we were both extremely immature, but still, the experience has stuck with me).

3. If he isn't interested, how do I make my getaway with at least some dignity intact?

Other possibly relevant details: he's male (duh), I'm female, both late 20s. Throwaway email: [e-mail]

posted by anonymous to Human Relations (16 answers total)

Personally I believe that the previous invitation to his party is a good sign. You ask why he would invite you if he was just going to neglect you, but there are good things at a party; good food (which he was busy preparing), other people worth meeting, and assorted entertainments which you could enjoy. Take this as a sign that he does have some interest in you. Go ahead and ask him if he would be interested in knowing you better (that is a delicate way to put it, as compared to, so, wanna f*ck?).

People often warn that it is risky to attempt a personal relationship with coworkers because they will still be your coworkers even if the relationship fails, and it could get awkward, and even if the relationship doesn't fail it could lead to office gossip. But then, there are only a limited number of situations in which we meet people and work is a major source of personal contacts. We have to make use of what we have. These things can work out. And even if they don't work out, you can be mature about it, and it doesn't have to be a problem.

So, what if he tells you he isn't interested? You could say something such as, OK then, see you at work. But I think he's interested.
posted by grizzled at 8:41 AM on September 16, 2010

Ask him for a drink, after work or somesuch. Then at the end of that, ask him if he wants to do [some date-y activity some other evening]. Things'll unfold, or not. My guess, he invited you to his party to show he was interested and that he has cool friends, then didn't pluck up the courage to be more explicit, and partly hid behind perfectly-legitimate-but-slightly-craven activities like foodfaff. If that reading's wrong, no loss in post-work pints.
posted by YouRebelScum at 8:47 AM on September 16, 2010

You need to do this if for no other reason than practice. If he isn't interested in you, who cares? There are millions, if not billions of people who, if introduced to you, would not be interested in you romantically. If he turns out to be one of them, that's life.

Romance is a game, you have to actively participate in it if you want to get anything out of it. That means taking risks. When you think about it, what are you even risking here? A little disappointment, a little embarrassment?

Ask him to go out for a drink. While having the drink, make a point of casually touching him on the hand, shoulder, or knee as you converse. See how he responds. You may not have to say a thing.
posted by hermitosis at 8:48 AM on September 16, 2010 [2 favorites]

I managed to come up with a legitimate excuse to suggest that we go for a drink while hopefully not forcing the implication of anything other than friends in advance.

You should bring up the implication of anything other than friends in advance. It is way easier to ask someone out on a date than to steer the conversation into "I'm interested in you territory" which is likely to be awkward for both of you. Forget about doing that. Instead, you should make sure you flirt. Act like you are having the best time ever. Smile a lot. Touch his arm a few times on a flimsy excuse. Be confident. A couple of days later (if you don't hear from him first), send him an e-mail saying "I had a great time with you on Thursday! I would love to go on a date with you sometime. How about dinner at $Casual_Restaurant on Wednesday?"

If he wants to go on a date with you, you have nothing to fear! If he doesn't, he's probably going to be a bit more mature about it than the dude from 10 years ago. Good luck!
posted by grouse at 8:53 AM on September 16, 2010 [1 favorite]

Definitely agree with the drinks and a little (not a lot) of alcohol as a lubricant. A followup invitation to your place to watch a movie or similar would be a pretty clear next step to greater intimacy (even if it's just sharing embarrassing childhood stories over a bottle of wine). That could be the same evening as your drink date.
posted by L'Estrange Fruit at 8:59 AM on September 16, 2010

"Hey, I'm going to (a thing) Friday. You should totally come too, it'll be awesome."

If he does, then congratulations, you are now on a date.

If he doesn't, then oh well.

If he does, and wants to bring other people, oh well.
posted by FAMOUS MONSTER at 9:06 AM on September 16, 2010 [3 favorites]

You should bring up the implication of anything other than friends in advance. It is way easier to ask someone out on a date than to steer the conversation into "I'm interested in you territory" which is likely to be awkward for both of you.

I agree with this, it's easier to say "Hey do you want to go on a date?" and get a wishy-washy answer than say "Hey do you want to meet as friends?" and then get into a possibly awkward conversation about being more than friends. I also agree with L'Estrange Fruit that inviting him to your house alone is a pretty unambiguous signal, but you may also be sending a signal that you want to get physical right away if you do that so keep that in mind.

If he isn't interested, how do I make my getaway with at least some dignity intact?

Well he's not an actual coworker of your's, so you can mostly avoid awkward meetings if things end up getting weird, right? If that's the case and he isn't interested, just move on. If your crush on him makes just being friends with him difficult you do not really have a big reason to continue hanging out with him.

Honestly all of this anxiety around making the transition from friends to a relationship and worrying about it ruining the friendship or being awkward is why I purposely tried to stop wasting time on crushes. If you are she and quiet, and haven't dated in a long time, give online dating a shot if you haven't. It's much easier to find a lot of possible matches who are actually interested in you that way than by getting a crush on a random person and agonizing over what to do about it.
posted by burnmp3s at 9:07 AM on September 16, 2010 [1 favorite]

I think I've finally gotten up the courage to ask him out, but maybe it's a bad idea. Sometimes I think he might be interested in me but sometimes I'm not so sure; he's pretty shy and quiet (as am I) and I can't really read him.

Welcome to our world, heh, heh. And from that world a little advice. It doesn't matter if he is interested or not. You never really do know. Just ask, it will be fine. You can recover. Nearly every guy has been rejected. You end up forgetting the names of some of the women who have said no.

1. Do you have any suggestions for how to steer the conversation a bit more into "I'm interested in you" territory? Obviously I'm not going to make a declaration of undying love or anything but since I will still see him in professional contexts regardless of the outcome I'd rather not make this a completely awkward conversation. Also it's been a long time since I've dated anyone so I'd rather not come across as completely desperate.

Avoid the steering. Don't even worry about what you say. Just cover the flirting base. When he's talking, look him in the eyes and smile. And compliment him. Just stick to that plan. Smile, sustained but not creepy eye contact. This tells him you like him and it screams confidence! And it feels damn good to him. Even if he has a girlfriend he will have a much better view of you and will be eager to make it easy on you.

2. Is there something I'm missing here that makes this completely a bad idea? I'm terrified of doing this - the only other time in my life I ever asked someone out, he didn't answer at all and then avoided me for a month (this was more than ten years ago and we were both extremely immature, but still, the experience has stuck with me).

Again, you get over it so quickly. Trust me, the guys have been there.

Smile, eye contact, compliment. It works for both sexes.
posted by Ironmouth at 9:10 AM on September 16, 2010 [3 favorites]

Oh and the touching is good too. I always wonder if the woman is into me if she start's touching me.
posted by Ironmouth at 9:11 AM on September 16, 2010 [1 favorite]

> he invited me to a party he was throwing that he didn't invite any other "work-related" people

>We have lunch together one-on-one about once every two weeks - he initiated this

He's interested in you; the problem is that he's as shy as you are.

As others have written-- touch him, smile at him, use sustained eye contact while touching and smiling at him.
posted by darth_tedious at 9:30 AM on September 16, 2010

The moment of contact between two potential mates can hang in the atmosphere deliriously and dauntingly like a gathering storm... a storm that may or may not strike ground.

This moment also hangs about in one's mind as one over-imagines every little moment that it could happen.

I'm picturing him at the party you were invited to saying to himself in his mind "I'm going to go kiss her/say X to her/hug her/whatever as soon as that guy walks away from her. No, no... as soon as she walks over to the kitchen. No... as soon as she finished that drink. No.. DAMN IT!"

I was totally this guy, always waiting for the perfect moment until "POOF" all the moments are gone and she's left to go home.

It's great to wait for the perfect moment when it all comes together but sometimes these things take Herculean effort to just do when you are shy.

It sounds like the chemistry is there so help it catalyze. Ask him "We have fun together, right? Do you think we like each other, because I think we do. What do think think would happen if we liked each other just a little bit more?"
If he answers "Yes. Yes." and "I don't know" then he really is shy and you should smooch him. Beyond that it's up to you to decide just how much shy you can take.
posted by No Shmoobles at 9:42 AM on September 16, 2010 [3 favorites]

1. Find a way to touch him on the arm early on. That's code for "I want you to kiss me later." Or at least that's how I take it when a woman does it to me. And, more generally, I would go with a strategy of flirting heavily on your date, rather than a strategy of steering the conversation toward how you feel about him.

2. Nope. There's no reason not to do this.

3. When this happens to me I just shrug and say "ah well, can't blame me for trying." There's no reason why this should involve a loss of dignity at all. That only happens if you react badly.
posted by Ragged Richard at 9:56 AM on September 16, 2010

I'm kind of hoping that once we both have a bit of alcohol inside of us my nerves will be calmed enough that I'll be able to take the conversation a bit beyond our normal how's-work-going and rant-about-the-boss type of conversations and hopefully express directly that I'm interested in him. Only, I have no idea how to actually accomplish this.

We always talk about work stuff; did you do anything cool these last few weeks that wasn't about work?

We always talk about work stuff; last week I went to saw/read/heard movie/play/book/magazine X and it sucked/ruled.

If that's too direct then there's stuff like "Speaking of Mary, she told me about this awesome band X that plays Y type of music; you like that kind of thing?"

if you're getting impatient with the uncertainty there's nothing wrong with a number of the above ways to send a more clear signal but you can also just work on making this more obviously a non-professional relationship by emphasizing non-professional things.
posted by phearlez at 9:57 AM on September 16, 2010

Some people do not date coworkers and are totally inflexible with this. I think it really depends on how closely you work together, the reporting structure (you should not have a manager-employee relationship and should be in totally different departments), and company policy. Another reason for not dating someone you spend all day with is that you spend all day with them and all night if dating, which can be a bit overwhelming for people who like some space.

Otherwise, go ahead and I think a dignified respectful non-drunken casual approach like asking them out to a dinner with just you two at a romantic restaurant would be best. And don't lose your composure if turned down or become icy cold or feel awkward. Smile and nod and say "I understand, it's fine," and carry on as you normally would. People turn down others for many reasons that they might not want to share - like not feeling ready after their previous one, having a sick parent, tying up a divorce, they have a crazy kink and only date people they know have it too, plans to move soon, their horoscope said so, they have a secret online long distance relationship with another Starcraft 2 player, pretty much anything so there is no reason at all to be offended.
posted by meepmeow at 10:39 AM on September 16, 2010

The lack of clarity is probably directly related to the periods of mutual staring-at-your-plates you say you have experienced.

He may be thinking, "well if I say X, she might think I'm totally coming on to her, and I would hate to be seen as someone who easily confuses legitimate professional socializing with something else."

The next time you want to do something with him, I suggest you be pretty clear that you're switching codes from work-ish-socializing to "this is a date". Even if you both are as cautious as can be, a little very clear communication can go a long way.

Bottom line, you're both already sending tons of signals, doing plenty of "steering" and hoping the other will catch on. Time for someone to do a little clear communication and make a (small) declaration. "Let's think of this one as a date" is not the same as "let's jump into bed" or "let's get married and have 8 children" and if this guy is as sensitive as you suggest, he'll totally get that.
posted by mikel at 6:26 AM on September 17, 2010

The answer to no 1 is to flirt. And flirt. And flirt. Flirting is the grown-up version of playing. You don't play with someone you don't like. Like the other posters have said, touch his arm lightly, laugh at all his jokes, point your feet towards his. "Accidentally" bump his knee with your knee from time to time. If he likes you back he will flirt back, or at the very least, he won't cringe from your touch.

I personally find declarations of "I am interested in you" somewhat odd and awkward. If someone said that to me, I would be like, um, yes, um, and now, what? (while silently thinking, yes, I kinda like you too and I would be interested in seeing where this goes, but you have put this fact to me so awkwardly and bluntly that I don't really know how to react). The best dates I had were those where we were both flirting with each other and enjoying ourselves the entire night, and not those where the guy declares out of the blue, "I am interested in you."
posted by moiraine at 10:19 AM on September 17, 2010 [1 favorite]