How do I go from friends with my male classmate to a relationship?
June 12, 2014 1:15 AM   Subscribe

It has taken me two years to get over my ex-boyfriend, and now, in graduate school, I finally, finally met a guy classmate whom I think could be great boyfriend material. He is kind, sweet, super intelligent, and not to mention pretty good-looking. We've spent a bit of time together on projects and study together occasionally, and over the past few months I've really developed some feelings for this guy. The trouble is, I am quite shy and not very good at flirting, so I've tried to initiate contact by organizing study get-togethers, asking him questions on Facebook, etc. I don't want to seem clingy or weird by initiating all this contact though. As for me, people have said I'm pretty, kind, intelligent, blah blah blah. I'm at a point in my life where I would like to find the right man for me and settle down, and I think this guy could be it. Unlike my previous relationships in which we met online, with this guy, I've developed a friendship and my feelings have grown from what I've gleaned from his character and interactions with his family and friends. I really like him, and I don't want to let this one go. Do you have any advice for how to maybe hint to this guy that I like him?
posted by enantio to Human Relations (30 answers total) 7 users marked this as a favorite
"Hey Fernando, I really like hanging out with you. Wanna go on a date with me on Friday night?"

Hasta lasagne, don't get it on ya.

Best of luck and let us know how it goes!
posted by smoke at 1:24 AM on June 12, 2014 [7 favorites]

Once again, smoke is perfectly correct.

Just ask him out.

Adults do.

It's the only way to know for sure. There may be two seconds of uncomfortable.....but compared to weeks or months of not's a ripping off of a band-aid..

Seize the day and do it!

And good luck. It's hard, nobody is saying it's easy. It's terrifying, of course.
But it's harder not knowing.
posted by taff at 1:28 AM on June 12, 2014 [2 favorites]

Response by poster: Thanks for your answers smoke and taff! However, I've always been taught not to ask a guy out. I know it's the 21st century and all but I still ideally would like the guy to make the first move. It's not as if I've received unequivocal signals that he likes me either; otherwise I might consider asking him out to coffee or something. In fact I don't think he sees me as more than a friend. How do I hint to him that I like him so that he (if he likes me) will ask ME out?
posted by enantio at 1:37 AM on June 12, 2014

Tell him, "Hey, I enjoy hanging out with you. You should ask me out on a date sometime."
posted by Arbac at 1:41 AM on June 12, 2014 [28 favorites]

However, I've always been taught not to ask a guy out. I know it's the 21st century and all but I still ideally would like the guy to make the first move.

I apologise for not answering the question. I will attempt to do so now - some guys are not very adroit at picking up signals, and may be just as shy/wanting the other person to ask them out as you are. Therefore, you have to make it crystal, crystal clear that you are a 'sure thing' when it comes to asking out. Ways to do this include: complementing them on their appearance at least semi-regularly, touching them a lot, mentioning how single you are all the time, and how you would love to be asked out on a date, suggesting activities ("I'd love to go to exhibition, but I don't have a date... *meaningful look/eyebrow waggle*, describe your perfect boyfriend but with very specific qualities that apply only to them "I would love to get a boyfriend doing the same kind of study I am, who's about 6 foot tall, wears jeans a lot and like listening to the same band you listen to all the time"), 'accidentally' brushing against them, resting your foot on theirs.

Does all that sound ridiculous and uncomfortably and kind of weird and forcefully flirty? It is ridiculous, OP. If you want to start a relationship based on strange rituals and reading-between-the-lines guesswork and gender exaggerations, go for it. Personally, I would go for honest, mature communication between two adults - i.e I start relationships the way I want my relationships to continue. And clear communications, a sense of equality, a willingness to say something a little bit uncomfortable, being prepared to be vulnerable, being courageous, being honest, that's all very important to me.

Know OP, your view will write off many, many good men who would make terrific boyfriends, for no very good reason. Further, the 'traditional' gender attributes you value in potential partners, may not make you so happy when you are in a relationship. Take some ownership of your feelings and responsibility in relationships; don't outsource it, I urge you.

This is nothing to do with the 21st century - you know, I know it - I would think carefully about why you value and want him to ask you out, and what you will get out of it. Follow the ridiculous tips above if you want - I had girls do that to me when I was a young man and eventually figured it out and asked them out. But there was a lot of guesswork in those relationships even after the ask-out, and they did not work out for me in the end.
posted by smoke at 1:55 AM on June 12, 2014 [56 favorites]

Data point: My wife is the one who asked me out.

In fact I don't think he sees me as more than a friend.
It could be that he sees you as a friend, but will warm up to you once he knows that it's a date, and he'll start parsing you differently.

Be brave!
posted by sebastienbailard at 2:14 AM on June 12, 2014 [3 favorites]

You could ask him on a very obvious date without calling it a date (come over to my house and watch a movie with me this Friday!) and then leave it to him to make a move. But then if he doesn't make a move where does that leave you? Wonderin'. Smoke's is still your best bet.
posted by Potomac Avenue at 2:46 AM on June 12, 2014 [1 favorite]

I still ideally would like the guy to make the first move.

Okay, but one way to think about it is that if you're going to be doing things equivalent to the Victorian dropping of your handkerchief, you actually are making the first move.

I'm not snarking or nit-picking, I'm pointing out that much like the women in Jane Austen novels who went through wild machinations to be at the same ball as the men upon whom they set their sights, you're making complicated plans just to get this guy to pay attention to you.

It's the same thing as making the first move, except instead of just asking him out on a date, you're making things overly complicated and you'll twist yourself into knots planning elaborate ruses in order to gauge his interest.

I understand that you don't want to make the first move, but I want you to see that by doing all these other things, it's exactly what you're doing. Except your method is a lot more drawn out, confusing and complicated.

All of which could be avoided by actually asking him to go on a date with you.
posted by kinetic at 2:48 AM on June 12, 2014 [18 favorites]

Knowing the the infuriatingly focussed mindset of graduate students, it is possible that he is misinterpreting your invitations to study sessions as an indication you want to focus on work!
posted by rongorongo at 2:49 AM on June 12, 2014 [1 favorite]

It's not as if I've received unequivocal signals that he likes me either; otherwise I might consider asking him out to coffee or something.

Well, he clearly likes you, or he wouldn't be spending so much time with you; what we don't know is whether he likes you in a romantic way. But that doesn't prevent you from asking him out to coffee, does it?
Friends have coffee together all the time, coffee is not a date. So maybe that can be a gateway towards an actual date? It seems to be within your 'rules'.

Ask him out to coffee. See how that goes. And he may very well ask you out on a date soon after. Or he may not, but then you're no worse off than you were before.
posted by Too-Ticky at 3:23 AM on June 12, 2014 [2 favorites]

Worst case scenario, you ask him out, he refuses and starts avoiding you. If this is not acceptable then don't ask him out.

What to do then? Invite him over for a movie (Potomac Avenue's suggenstion), start casually but make sure he understands you're open to something else. If he doesn't make a move, maybe he's not interested, but you keep him as a friend. If he's interested, but he's shy and doesn't make a move, he'll probably let you know in some way, maybe he invites you back, maybe he comments on what a great movie night you had.

Don't rush.
posted by dfreire at 3:29 AM on June 12, 2014

Ok, 20 odd years ago I my love interest and I were part of a big group of friends.
One day I said to him "hey, we should go see a movie, there's some good ones on right now." (Thinking: If he's interested, he'll jump on that)
He said, "cool, good idea. How about movie X?" We decided on time and place. Then I waited. We were, after all, officially friends and often did things in groups. I figured if he was interested in me, he wouldn't ask any other people to join us.
Movie night came and he came solo! Yay!
Then afterwards we had a drink and I took his hand under the pretext of comparing hand sizes. According to my husband, that was the first time he realized I was interested.

It was terribly clunky and I was 19. Hope it helps anyway.
posted by Omnomnom at 3:29 AM on June 12, 2014 [10 favorites]

I completely understand the desire for him to make the first move, but... well, one of the touchstones of a good relationship is being able to comfortably and directly ask your partner for something. Might as well start doing so from the beginning. It'll be nervewracking, but no more so than dropping hints for weeks on end and hoping he figures it out.

And, seriously, if he isn't interested in dating you, he'll likely either continue to be oblivious, or he'll ignore your signals and hope you get the hint. And so it'll go on for longer than it needs to, and perhaps you'll start obsessing and idealizing as so many of us do with unrequited crushes, and it'll just be harder to get over if he doesn't return the interest. He knows you well already, and you can't make him feel differently from how he already feels. You can't flirt and hint your way into a yes if his answer is no. Might as well ask and find out the answer now.
posted by Metroid Baby at 4:21 AM on June 12, 2014 [5 favorites]

Ask him out. It's the only way of knowing for sure if he's interested. If you don't ask him out, he might not ask you out because he's not interested, or he might just be oblivious, and you'll never know which it was. You have to take opportunities when they present themselves if you want to get what you want.

Also, this is pretty much exactly how my relationship started. I asked him out. We're getting married next year.
posted by quaking fajita at 4:49 AM on June 12, 2014 [1 favorite]

If you really really do not want to ask him out on an overt date, you can suggest increasingly non-study-partner activities for the two of you and hope that the natural chemistry of these outings leads you where you want to go. Activities that involve a little more adventure, a little more dressing up, a little more intimacy or a little more domesticity are all good for getting him to see you in a different light than he already does.

Obviously, this is still dating, just with a side order of plausible deniability.

Sooner or later there will come a time when one of you has to make a definite move. And depending on circumstances, that may still need to be you. However, if you've been on a few crypto-dates you'll probably at least have a better sense of how your advances will be received.

(Credential: Various not-officially-a-date activities followed by me making a more overt move is how I got together with my husband.)
posted by shattersock at 5:08 AM on June 12, 2014

I'm at a point in my life where I would like to find the right man for me and settle down, and I think this guy could be it . . . I really like him, and I don't want to let this one go . . .

Ok, first, definitely don't tell him this.

It is awesome that you're feeling ready to get back into dating, but don't mistake the attraction and interest you're feeling for some sort of expectation that this guy is "the" right man for you. This is great news, OP - because there isn't just one right man out there for you, there are likely many, many men who could be a right man for you.

I say this to just encourage you to not put too much pressure on this interaction. It would be fantastic if you guys went out on a date, but if it doesn't work out, it isn't the end of the world. And putting too much pressure on it succeeding is basically a guaranteed way to make it not work out.

I won't chime in on any advice about the "how to get him to ask you out" bit because I agree with everything smoke and others said upthread. As a female, former grad student I would strongly encourage you to gather your courage and make the first move. Even if you do everything suggested upthread (which is the 21st century equivalent of fainting in some guy's parlor to try to get him to catch you) there are still many kind, sweet wonderful grad students who would not realize what you were trying to do. They might also be interested in you! But the way to explore whether you might have a relationship with this guy is to just reach out. If it seems too difficult to do in person, send him an email and say "Hey Name, I haven't ever done this kind of thing so I feel a little awkward asking this. I like you. Would you go on a date with me? I was thinking EVENT, DATE. OP". But in person is much better, if you can work up your courage. Good luck!
posted by arnicae at 5:12 AM on June 12, 2014 [9 favorites]

There is no way to manipulate someone in to asking you out on a date without, you know, being manipulative. Just ask him out and stop giving yourself lame reasons not to. What it comes down to is you're shy and don't want to face the possibility of rejection so you are clinging to some outdated philosophy about gender roles.

I used to be you. Then I made a list of things I was afraid to do and started checking them off that list. First on that list was to -for the very first time in my 25 years of life- ask a man on a date. I had a particular one in mind. Someone I thought could be The One but who didn't seem to be interested in asking me out. I asked him out. Ten years later he is laying in bed next to me right now, one of our babies is sleeping down the hall and the other is still cooking, going to be joining us in a couple months. We just celebrated our seven year wedding anniversary.

You can do this. Even if your story doesn't end in the way you want it you will grow as a human being and that is pretty great.
posted by teamnap at 5:41 AM on June 12, 2014 [9 favorites]

So I'm actually going to try to answer the question as is. I basically don't ask guys out. At least, I can't think of a time when I've straight-up asked a guy on a traditional date, and I don't really think I've felt the need or want to. I have messaged guys on okcupid first but that led to two nice first dates/meetings and nothing further. Right or wrong, here's how I look at it: in a perfect world, guys would still ask out women 50% of the time. Gender equality doesn't mean the woman takes on the pursuer's role more than 50% of the time. I think there is room in the modern world for people to prefer guy-asking, room for people to prefer lady-asking, and neither is "straight-up bad" or "traditional and sexist and wrong." I also think part if why women don't pursue as much isn't because of sexist patriarchal gender norms so much as because it is actually beneficial to the woman to gauge a man's interest, or because she's already getting offers and doesn't have to. I also think it's often that women do often flirt first or even plan "pseudo-dates" and this is fairly normal and accepted, but it is not often that women ask out, plan, and pay for a full date in a " wooing" sense. Like it or not, that is the world I see around me. So I'll try to answer the question as is. Even if it makes MeFi collectively goes.

Things I do when I want to be asked out:

Look really pretty around him. Dress more femininely.
Laugh a lot at his jokes.
Maintain eye contact.
Lean in close.
Tell mutual friends (yes, just like in third grade) that I like him and hope it gets back to him.
Be/act more confident, spunky, social and outgoing than usual- plan many things in big groups, go out a lot to events he might like or be at.
Compliment him.
Talk to him and just be around him a lot using any excuse.
Drink with him.
Swim with him.
Do dangerous/exciting/scary things with him.
Be slightly more vulnerable with him sometimes and gauge his reaction.
Touch my hair a lot.

Nauseating? Maybe. I dunno. There's probably more stuff I'm not thinking of. The SIRC guide to flirting is worth a read.

I will say that if a guy does not respond in kind in a certain window of time I tend to lose interest pretty quickly.
posted by quincunx at 6:09 AM on June 12, 2014 [4 favorites]

I've always been taught not to ask a guy out. I know it's the 21st century and all but I still ideally would like the guy to make the first move.

You can't have it both ways. If he wanted to ask you out, he would have. Done, not boyfriend material.

That line of thought only works if he's confident, knows your current dating situation and the stars align in such a way that he feels comfortable asking you out. For whatever reason, either he's not, he doesn't and they haven't.

It's also unfair because if you presume that he's going to do the asking out, he's also going to do the paying, and he may be broke, or frugal or what have you.

I'm at a point in my life where I would like to find the right man for me and settle down, and I think this guy could be it.

Cart before the horse. You don't know him well enough to jump to "THE ONE", as it stands right now, by your standards, he's not interested enough in YOU to ask you out.

There are plenty of great men out there, there isn't just ONE great guy for you. This is just a guy you're attracted to and who appears on paper to be the kind of guy you're into.

Step back, chill out.

Now, what to say to him to assess if he is available to date, and is into you for dating?

"Reynaldo, we've been good friends for over a year. I think you're a great guy and I'd love to date you, if you're open to that."

Other than turning to love spells, there is no secret thing you can do to get him to suddenly notice that you're available and interested and that you want him to ask you out.
posted by Ruthless Bunny at 6:33 AM on June 12, 2014 [3 favorites]

Other than turning to love spells, there is no secret thing you can do to get him to suddenly notice that you're available and interested and that you want him to ask you out.

I almost 100% agree with RB here except:

Are you dressing cute? Wearing makeup? Fixing your hear? Perfume? Push-up bra?
Laughing at his jokes?
Can you relax your body? Turn your wrists out a little and relax your energy into your hips. Smile.
Respond! Respond from your self, your body; get out of your head a little and respond to whatever energy he's putting out.

If he STILL doesn't bite then you'll just have to mentally move on. Just like Ruthless Bunny says, you can't have it both ways, if he wanted you by now and was a 'make it happen' kind of a guy then you'd be dating already.

PS. Women ALWAYS make the first move, BUT they do it by signalling that they are interested - by doing a little 'looky-looky' or adjusting their appearance or whatever. Sure a guy says 'hi' first but by then the woman has already chosen him. A guy who pops up out of nowhere without giving the woman a chance to once him over first is odd at best, and creepy at worst.
posted by St. Peepsburg at 7:21 AM on June 12, 2014 [2 favorites]

Just FYI, there is a subset of guys who are going to remain clueless to all but the most direct overtures. All the makeup and hair-twirling in the world will not change that. If you are unwilling to be as direct as "I think you should ask me out" then just be aware that there is a subset of men who will never date you because you didn't use your words. That's absolutely fine but would have been sad in my case as I'd never have gotten together with my husband.
posted by DarlingBri at 7:34 AM on June 12, 2014 [6 favorites]

Just say, "hey do you want to get a drink sometime?" It's not as formal as asking him to go on a "date" but enough to show you want to hang out with him outside of school related things. I was also hung up on the idea of the guy making the first move, but then one day I asked a guy out and it was sooo refreshing, EVEN when he said no. Kind of funny, but just doing the asking felt soo empowering.

On the other hand, I was the one to first ask out my now boyfriend and he hasn't stopped calling me since that first date. :)
posted by monologish at 7:53 AM on June 12, 2014 [1 favorite]

If you are afraid of rejection but want to dip your toe into the pool of Being Assertive In Order to Get What You Want, there are many things you can do to hint a little more directly while remaining on the side of plausible deniability if it turns out he's not so into it. I agree with everyone upthread who suggests asking him for a movie or coffee or whathaveyou. Do that! If you must, ask him via text or chat after a glass of wine (but no more than one!!).

One tactic that worked well for me in college was this:

Me: "Hey [cute friend], wanna come over and study for the exam? I can make some dinner [rice and beans. don't get fancy]."

The studying happens, dinner happens, and we, both painfully introverted and shy, gradually warm up and relax and the 'isthisadateisthisadate' inner monologue winds down.

Cute friend: "Welp, it's pretty late...I better get going."

Me: "No! Don't go."

Cute friend: "What? Why not?"

[several seconds of delicious awkwardness]

Me: "Because..." [blushing terribly, and finally it seems to dawn on him what I'm doing]

Cute friend: "Oh!" [kisses me]

We dated for a while after that, but not too long, because what we liked about each other in school didn't translate so well to post-grad. YMMV, but take it one step at a time and don't put too much weight on this guy being "the one."
posted by magdalemon at 7:57 AM on June 12, 2014

I know it's the 21st century and all but I still ideally would like the guy to make the first move.

And what if he's the kind of guy who thinks "hey, it's the 21st century, I'd like a woman to make the first move"?

Does that mean he's not actually "good boyfriend material"? Or does that mean he might still be "good boyfriend material," but you'll never know because you won't ask him out?
posted by scody at 9:17 AM on June 12, 2014 [1 favorite]

The rules of flirting are four:

Eye contact, smile, compliment, light touching.

If you must practice on a friend or a pet or a plant, do it.
posted by Ironmouth at 9:29 AM on June 12, 2014 [4 favorites]

This guy has seen and been with you as much as you've seen and been with him. He might already sense that you like him and is still doing nothing about it. He might have a crush on somebody else. He might have a crush on you. A little extra make up and a flirty smile might be all he needs to know to ask you out. It might put him off and you could find him turning down furture get togethers. You could spend months awkwardly flirting together with nobody making any further moves.

Once you've realized that you like somebody and actually want them to like you, you become vulnerable no matter how you choose to approach it. It kinda sucks but it's the way it goes. So, even if you don't explicitly make the first move, you can still be rejected. It could just potentially drag the situation out much longer than either of you want and be as vague and confusing as your attempts to woo him.

Who knows what he's thinking but you know you like him, so you need to do something about it. Take the long, vague route or make it simple and just ask him out. You'll most likley get to the same result either way. Starting with a drink or something to eat after your next study session is a great idea. You can think of it as a baby step, pre-date, date, if you need to.
posted by AtoBtoA at 11:40 AM on June 12, 2014 [3 favorites]

The philosophy behind this excellent answer to one of your previous questions seems applicable here -
"So it seems to me that it'd be better to figure out realistic coping strategies, in case you do end up getting hurt, rather than abstaining. I can sympathize with wanting a perfect shield that can protect you from all of the potential harm and scariness that comes from letting yourself trust someone, but there really isn't anything in the world that can magically protect you from the possibility of getting hurt while you go out and live your life. Better to figure out ways to know in your bones that you can survive whatever the world throws at you than to create filters and imaginary shields that might not even protect you from what you're hoping they will."
You gotta go out on a limb a little bit.
posted by sestaaak at 1:43 PM on June 12, 2014 [1 favorite]

FWIW, I have never worn dresses or skirts, used makeup, had long hair, worn push-up bras. Yet I've always had a boyfriend whenever I wanted to have one. So no, it's not that.
posted by Too-Ticky at 2:30 PM on June 12, 2014 [4 favorites]

One consideration is that he's consciously or unconsciously decided not to hit on colleagues, for a variety of practical and ethical reasons.

Which means when you say "Do you want to see a movie?", he'll think "Yay, a fellow Godzilla fan!". And not "This is a date."

Try founding your relationship on open, clear communication, and ask him on a date.
posted by sebastienbailard at 7:30 PM on June 12, 2014 [1 favorite]

Response by poster: Thank you all so much for your answers!
posted by enantio at 12:01 PM on June 13, 2014

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