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How to make a move on someone I've been waiting to approach?
July 21, 2012 11:41 PM   Subscribe

How do I approach a castmate I've developed feelings for? We've been working on a show together for about a month, and I've developed an attraction to him. I immediately determined I should wait until the show closed to make any obvious moves, but I'm not sure how to do it.

He's friendly and playful and teases me, but it's unclear whether he's interested. In addition, I recently learned that he's rather awkward at approaching women, having been in a years-long relationship from about age eighteen until a couple of years ago. (He's in his late 20s.) It seems plausible that he wouldn't make a move regardless of possible interest. He may not even quite know how, odd as that sounds.

I asked him to dinner about a week into rehearsals because it was clear we had a lot in common. We walked about twenty minutes, went to a shop, got coffee, and had dinner. He didn't offer to pay or anything, but he let us sit and talk for half an hour before ordering because "the company's good." After a long dinner, he walked me home because the area is a bit sketchy, but he sat on my steps with me for about twenty minutes so we could keep talking. All told, we spent five hours together. It was very relaxed and touchy-feely - no holding hands, but I got good vibes. (Again, though, we're theatre people. Touching may mean nothing - we touch a lot in our show.)

In the last few weeks, I've been flirting a lot - teasing him, little touches, all my best moves. Problem is, theatre people use banter and teasing and touches to make friends and establish rapport among the cast. So this is likely to be seen as friendly, not hitting on him. I'm also a hugely bubbly, energetic person. And my character has a crush on his character. So I think it may all be getting lost in the noise, so to speak.

Anyway, the show closes pretty soon. I want to have a plan. There's likely to be making out at the cast party, which probably will just mean fun with friends to anyone involved (including, usually, me - which he knows). I'm not sure how to make it clear that I'm attracted to him and not just as a friend / pair of lips. I also don't want to spook him or make things awkward, as it's likely we'll work together again at some point in the next few years (college theater, nothing professional).

So, how do I be delicate about this without leaving him guessing? Because he's said (and shown) that he's not too skilled at guessing.
posted by lemoncakeisalie to Human Relations (35 answers total) 2 users marked this as a favorite
 
(and I'm not too good at delicacy)
posted by lemoncakeisalie at 11:42 PM on July 21, 2012


I'm sorry if I was unclear. I'm not a professional actor, and neither is he. He's not my colleague - it's a college theatre group, and relationships develop all the time between cast members. (I can think of three right off the top of my head - I've also had a friends-with-benefits situation develop with a cast member.) So it's really not a problem.

I see no reason to be professional about my hobbies after it can't harm the final product (the show).
posted by lemoncakeisalie at 11:54 PM on July 21, 2012 [2 favorites]


Plan: After show is over, "hey, now that the show is over, do you want to go on a date with me?"

I think a lot of the other details/stuff you're mentioning here are red herrings or irrelevant. All you really need to do is ask him out, and make it clear you mean on a date. His answer will let you know the next step.
posted by so_gracefully at 11:56 PM on July 21, 2012 [22 favorites]


Plan: After show is over, "hey, now that the show is over, do you want to go on a date with me?"

I think a lot of the other details/stuff you're mentioning here are red herrings or irrelevant. All you really need to do is ask him out, and make it clear you mean on a date. His answer will let you know the next step.


I figured I'd throw all my spaghetti at the wall. :)

Is there a way to make my interest clear without putting him on the spot like this? Perhaps ask him to hang out again and just play it by ear?
posted by lemoncakeisalie at 11:58 PM on July 21, 2012


Or is that the wuss answer? :)
posted by lemoncakeisalie at 11:59 PM on July 21, 2012


No, not "wussy" at all. It will make you seem like a normal human being, because who says "go on a date" anymore?

Just say, "would you want to hang out sometime?" It means the same thing, but there's plausible deniability in case he's not into that. If you don't want to do it face-to-face, you can even add him on Facebook and go from there. That's the lowest-pressure way to move into someone's orbit.
posted by drjimmy11 at 12:16 AM on July 22, 2012 [1 favorite]


Yeah, the above plan's pretty much the way to go. Just be sure when you're making the actual pitch, you've got the smile, eye contact, body language, etc., all cued in, just like a good actress.

Seriously, for anyone in a decent place emotionally, getting a sincere invitation from an attractive member of their preferred gender is *never* bad/awkward; and if it is, that's telling you he's not ready for anything at the moment, which you'd just as well find out up front.
posted by 5Q7 at 12:17 AM on July 22, 2012 [3 favorites]


He might be wussy but I'd he really liked you, he'd have approached you already.
posted by discopolo at 12:41 AM on July 22, 2012


If you don't want to do it face-to-face, you can even add him on Facebook and go from there. That's the lowest-pressure way to move into someone's orbit.

We're already Facebook friends and interact a decent amount. We've also gone out twice in groups for dinner and/or drinks with some of our castmates.

Just be sure when you're making the actual pitch, you've got the smile, eye contact, body language, etc., all cued in, just like a good actress.

Seriously, for anyone in a decent place emotionally, getting a sincere invitation from an attractive member of their preferred gender is *never* bad/awkward


This made me grin and feel extra cute for some reason. :) Thanks.

I'd he really liked you, he'd have approached you already.

This had occurred to me - but then, I'm quite a go-getter, I really like him, and I've kept mum. It could be he's being professional for the same reasons I am - to avoid harming our stage chemistry, which is warm and very natural.

I'm a believer in the whole He's Just Not That Into You thing, but I think I can't tell until the show ends. Is that naïve or realistic?
posted by lemoncakeisalie at 12:48 AM on July 22, 2012


[Lemoncakeisalie, moderator here. No need to respond to every comment; Ask Metafilter is not really meant to be a discussion space, so unless you need to clear up a misunderstanding or answer a question, it's better to just relax and take in the suggestions.]
posted by taz at 1:21 AM on July 22, 2012 [3 favorites]


Is there a way to make my interest clear without putting him on the spot like this?

You make your interest clear by making your interest clear. Not by hedging around and hoping he's a mind reader. Just ask him out! On a proper date and everything so he knows what you're after.

I'm a believer in the whole He's Just Not That Into You thing, but I think I can't tell until the show ends. Is that naïve or realistic?

When you ask him out on a proper date type thing if he's not into you he will say no. Then you will know for sure.

Stop overthinking this and making up drama, just be straight forward and well intentioned then get on with whatever happens afterwards.
posted by shelleycat at 2:04 AM on July 22, 2012 [6 favorites]


Is there a way to make my interest clear without putting him on the spot like this? Perhaps ask him to hang out again and just play it by ear?

It's great when relationships emerge naturally from gradually escalating subtle cues. It's romantic, exciting, painless, and the complete opposite of awkward.

However, it's not the usual case, and waiting for it to happen is a path fraught with ambiguity, doubt, and anxiety that's almost certainly worse than just asking.

If you really want to let someone off the hook in advance, give them two options: a specific agreement to do something as a couple plus the polite excuse that you think won't be awkward. In this case, "Hey, would you like to go out with me on Saturday? Or do you think it's better to remain just friends?"

Not giving them the excuse is probably the better way to probe their actual feelings about you (perhaps involving slight and/or mutual embarrassment), but giving them an out is a reasonable way to indicate you're aware they may not be into you and that you're OK with that.

The important thing is not to be ambiguous about the important thing, which is that this is a date and you're going on it as a couple at a specific point in the near future. And ideally you've already worked out some options that would be pleasant for both of you.
posted by Monsieur Caution at 2:25 AM on July 22, 2012 [5 favorites]


Hey, $MALE, would you like to go out sometime? I fully understand if you'd rather remain just friends.

I get it about not contaminating your professional space, but even if this were a professional show there's no telling whether you'd ever work together again so I would consider it well worth the risk.
posted by tel3path at 3:15 AM on July 22, 2012 [1 favorite]


I think waiting until the show ends is a sensational idea.

Other than that, "Hey, I had a great time the other night. Wanna hang out again? Let's go grab dinner."

There's nothing complex here. You like him, he's acting like he likes you. Go for it. Good luck. Have fun.
posted by His thoughts were red thoughts at 4:20 AM on July 22, 2012


I think that there are three factors at play here:

1) Opportunity
Is he available? Or is he taken? You can generally figure this out by checking out the other person's Facebook profile, but some people are more private. A little more subtle snooping may be called for here.

2) Attraction
Is he attracted to you physically? It's quite possible he may like you, but "not in that way." When he's in a social situation and there are other attractive women present, do his eyes linger on you? Or is he scoping for other prospective targets? What is his usual behavior around other members of the cast - does he demonstrate the same degree of physical touchiness that he does with you? Behaviors that differentiate how he acts towards you from how he acts towards other people are good signs, but try to be aware of wishful thinking/confirmation bias.

3) Seduction
Light touches are good. One-on-one coffee dates are also good. But actual seduction implies gradual escalation of the sexual element in your interactions. For example, you could try changing the venue for your one on ones "hangouts" from coffee in a public space to hot chocolate at your apartment. Gradually do things that are slightly more provocative. For example, watching a movie together in your room is one example. Another might be asking him to reach something on a high shelf for you, but not really moving out of the way (so he has to put his arms around you to get to it). These are not perfect examples (the approach should be tailored to the personality of the individual in question) but generally good strategy is to gradually escalate the sexual context while still maintaining plausible deniability, right up until the moment when one of you makes an overt move.
posted by wolfdreams01 at 5:54 AM on July 22, 2012 [1 favorite]


I cannot argue enough against "hanging out" (and for explicitly mentioning "date"). This article has the genders flipped and is couched in more gender-normitude than I care for, but it covers the problems I have with those damned kids today. (Note point #4 and "they avoid rejection or failure by not asking women out on dates".)

Ask.mefi is full of answers stating that you should be straightforward and clear that what you think of as dating should also be conveyed to the other party. Here's another one: ask him out. On a date. Make sure he knows you're asking him out on a date. Be open to possibilities. Be clear there's no pressure.

Have fun.
posted by cardioid at 6:00 AM on July 22, 2012 [3 favorites]


"Hey, I had a great time the other night. Wanna hang out again? Let's go grab dinner."

You already did hang out. You already did grab dinner. How's that working out for you? Ask him on a date.
posted by Rock Steady at 6:25 AM on July 22, 2012 [5 favorites]


I asked him to dinner about a week into rehearsals because it was clear we had a lot in common.... He didn't offer to pay or anything

Um. YOU asked HIM out. Did YOU offer to pay? He might've gotten more of a hint if you had.

Is there a way to make my interest clear without putting him on the spot like this?

I think there's another disconnect here. I think what you really mean to ask is "Is there a way to make my interest clear without being embarrassed that I'm interested if it turns out he's not?"
To use theater terms, it sounds like you want to "set the stage" for him to ask you out, for him to seduce you, for him to sweep you off your feet. And you're hoping against hope that the reason he hasn't done it yet is that he's awkward around women. That's a nice narrative, but it most likely isn't going to go down that way.

Ask him out on a date. If you beat around the bush and maintain plausible deniability for yourself, your next Askme will be "well, I asked him if he wanted to hang out sometime and he did, and we did....but we only ended up hanging out. I dropped all kinds of hints by flirting with him (even though theater people flirt with their cast mates all the time), hesitating to pay the bill ( even though I asked him out) and ever so slyly brushing his hand with my hand. He didn't even hold my hand! How can I figure out where I stand with him?"
posted by vitabellosi at 6:34 AM on July 22, 2012 [11 favorites]


The worst thing that could happen if you ask him out "on a date" is that he'll refuse.

The worst thing that could happen if you hinted around and flirted and hemmed and hawed about dating without letting him know what you really mean is that you'll spend a ton of time, energy, and emotion wondering if he wants to date you or not without actually finding out, which could drag out a very long time.

Which outcome would you prefer?
posted by xingcat at 7:20 AM on July 22, 2012 [5 favorites]


Ask him to join you at something you are both interested in (movie, reading, exhibit, pub quiz....), you don't have to say point blank: "Let's go on a date"
posted by brujita at 8:47 AM on July 22, 2012


Speaking from experience... are you SURE he's not gay? Maybe is but isn't willing to admit it? You are both so young and this is the time when people are still figuring themselves out. I am not trying to offend anyone. Just... think about it.
posted by I_Love_Bananas at 8:48 AM on July 22, 2012


are you SURE he's not gay?

Yes, I'm sure. Since I'm bi, things like this tend to come up in conversation pretty naturally. He's made out with men and women and the men did nothing for him.

Thanks for all the great advice so far!
posted by lemoncakeisalie at 9:16 AM on July 22, 2012


Sorry to be the one to say this, but it sounds like he's either not interested or not ready for a relationship. You already went on a date (you asked him out). If he hasn't pursued it further, there is probably a reason for that. It could be a reason entirely unrelated to you and probably is.

But I think most men are able to ask someone on a date if they really want to go on a date, especially when they know the woman is interested. Keep yourself busy with other things for a few days. If you give him the opportunity to miss you he might ask you out.
posted by luckdragon at 9:40 AM on July 22, 2012 [1 favorite]


discopolo: "He might be wussy but I'd he really liked you, he'd have approached you already."

Or maybe he also thinks it would be a good idea to "wait until the show close[s] to make any obvious moves". As others have said elsewhere on AskMe, make the person you're asking out reject you if they're not interested — don't preemptively do the rejecting to spare them work and you embarrassment.

Another vote for being cheerful, low-pressure, and absolutely clear that you're asking him out and inquiring as to whether a romantic relationship is a possibility.

The invisible Magic 8-Ball I'm looking into says SIGNS POINT TO YES, fwiw.
posted by Lexica at 10:11 AM on July 22, 2012 [2 favorites]


Aren't you going to the cast party? I thought that was the whole purpose of cast parties.
posted by cmoj at 11:31 AM on July 22, 2012 [3 favorites]


Yeah, if he's as awkward/bad at this as it sounds, you don't have a way to get the answer/clear answer you want with outputting yourself out there and making it clear that you're asking him on a date. Or you could really ramp up the flirting, but again, you might, like, have to try to kiss him in a way that's unmistakeable. You're not going to be able to avoid putting him on the spot or be able to leave him an out other than saying no or whatever you're calling it, which I think really means you want to avoid putting yourself out there and risking rejection.

The good news is, if you ask him on a date date and he says no, it's not the end of the world and you should be able to both go back to being friends.
posted by J. Wilson at 12:00 PM on July 22, 2012 [1 favorite]


Ask him out for dinner again, but this time, instead of chatting him up on the stoop, ask him up for a glass of wine. Alternatively, ask him over to your apartment to watch a movie. Prime cuddle op.

Even back in 2006, college kids weren't saying "date." No need to sound like a grandma. He'll get the hint.
posted by PhoBWanKenobi at 2:10 PM on July 22, 2012


Keep yourself busy with other things for a few days.

That's not really possible - we're coming up on the show, so we'll see each other about 24 hours weekly until mid-August. I'm not getting great vibes, but yeah, cast party is a possibility.
posted by lemoncakeisalie at 3:24 PM on July 22, 2012


Oh - another piece of information that may affect some of the answers.

His job is advising undergraduates. I live in a dorm (in a single). It feels awkward to invite him up. Other ideas in that vein?
posted by lemoncakeisalie at 3:25 PM on July 22, 2012


I disagree with other answers that insist you just explicitly say "date". I'm in favor of more subtlety and grace.

Keep inviting him to things where you two are alone, without ever uttering the word "date". Be casual about it, but make it pretty clear no one else is going. Make up something like "My friend just flaked on me, I have a spare ticket to this concert, wanna join me?" Keep up the flirting and commiserating on said occasions. If he's repeatedly going out with you alone and flirting back and talking more and more personal subjects, there is no possible way he isn't interested. At that point, the ball is on the goal line. Be bold, and tap it in.
posted by stroke_count at 5:54 PM on July 22, 2012 [1 favorite]


Go ahead and ask him up! You have privacy with the single.
posted by brujita at 6:14 AM on July 23, 2012


Ask him out for dinner again, but this time, instead of chatting him up on the stoop, ask him up for a glass of wine. Alternatively, ask him over to your apartment to watch a movie. Prime cuddle op.

The problem with this is that it does not address this concern of the Asker's:

I'm not sure how to make it clear that I'm attracted to him and not just as a friend / pair of lips.


In a world of FWBs and casual cast-party makeout seshes, the "Come up to my room and see what happens" approach still leads to uncertainty about the status of the relationship, even if freakytimes occur. If you want to have a romantic relationship with this guy, you have to tell him so in pretty explicit terms, otherwise your next AskMe will be, "I made out with this guy at a cast party. Are we dating or what?"
posted by Rock Steady at 7:30 AM on July 23, 2012


In my experience, some ambiguity is totally normal at the very beginning of college-aged relationships. The kissing strongly signals romantic interest; the hanging out and talking strongly implies that it's not just a hook-up. I'm not sure that relying on an explicit-dating model mostly used by older generations is a great idea here. It's pretty far outside the bounds of normal.

However, if he advises undergrads, are you sure he's even permitted to date them?
posted by PhoBWanKenobi at 7:58 AM on July 23, 2012


However, if he advises undergrads, are you sure he's even permitted to date them?

He advises undergrads at another university in the city, so I'm sure it's fine except for the possible weirdness for him.

Thank you all for the blunt wisdom! We've been flirting quite a bit over text today, which he initiated after a non-flirty text from me, so I'm working on it.

I'm planning to be casual, give him an option to get drinks as "friends or maybe [smile] not-as-friends? either is okay with me."

The show closes in mid-August. I'll keep this open and let you know how it goes then! Bye for now!
posted by lemoncakeisalie at 12:13 PM on July 23, 2012


An epilogue:

Show just closed. Two weeks ago, I got drunk, and he figured out I was into him. I acknowledged it and asked if we could talk after the show closed.

We discussed things yesterday, during the cast party. It was a warm and sincere discussion, and it felt honest and straightforward, no platitudes. We agreed that we wouldn't be a good long-term match, and he also explained that he still isn't over the seven-year relationship and isn't ready to casually date, so all that is out.

Afterward, we cuddled comfortably on the bench with his arm around me, just talking. Finally, the hostess came to tell us they were going to open director presents, so we had to go back to the cast party.

When she left, I knew it might be my only chance, so I asked if I could kiss him. He was speechless for a good three seconds (he apologized afterward and explained that it wasn't that he was unsure, just that it had taken him a moment to process what I'd said). We kissed for a long moment, definitely more than a peck, before going back inside.

I think we'll continue to be friends. I'll see how I feel. Here's hoping my crush fades post-show, because it's possible we could be sexual if that happens. But if one kiss is all I get, I definitely don't regret it! :)

Thanks for the advice.
posted by lemoncakeisalie at 4:29 PM on August 12, 2012


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