Gaining Perspective on Unrequited Something or Other
November 10, 2019 12:08 PM   Subscribe

When we were 21 years old, a friend had a crush on me and I rejected him. 12 years have passed, and we have kept in touch despite living thousands of miles apart. We've traveled together, were roommates for a time, etc. Neither of us has made a move since that one rejection, and I doubt he is interested anymore. But I am. I miss him a ton and fantasize about us being together. And then I get sad. Should I dismiss these fantasies or should I make a move?

How do I get out of this holding pattern?

I am trying to put this crush and these fantasies of being with him out of my mind and concentrate on the stuff that makes me feel successful and happy, like studying or applying to better jobs. I have also been working hard to make my own home and relationships as happy as possible, doing a TON of personal work, like therapy, and just plain nesting. I am single, and it is by far the largest source of unhappiness in my (overall quite good) life but am also very burnt out on dating apps and not actively dating.

One of the things that I've been working on in therapy is being more direct and truthful about what I want. And some people in my life have been unhappy when I've told them "no" or gone ahead and done the thing that's best for me regardless that it's less convenient for them. But being direct and truthful has been a very freeing experience despite that. I want to continue with this directness and truthfulness! In this case, does that mean making an explicitly romantic gesture?

And I am also taking some time off in the next few weeks (I'll have about 10 days off at the end of this month, including Thanksgiving), because I have a lot of "use it or lose it" PTO...

My friend invited me to come stay with him in his brand new condo and I'm so tempted to hop on a plane or jump in the car and do it during that time. This is not practical in any sense, I have a lot of fairly large expenses right now and my new dog is still getting settled in. But then there's a part of me that says, "but it would be so fun!"...and an even quieter, wilder part that whispers, "and what if you love him? what if you're throwing away love just to save a few hundred bucks and some hassle?"

The other issue is that I just don't know if he's interested, and at this point am pretty pessimistic. When we've stayed in the same place the last couple years, he's made a point not to share the bed with me (which we used to do, through maybe our mid-twenties -- although nothing ever "happened," it was completely chaste). He always pays, but I think that's just him being generous. He basically treats me the way he does a treasured sister. But we also get along like a house on fire, and it's so hard to separate out massive-friendship-chemistry-between-opposite-gender-heterosexual-people and romantic chemistry or interest. Like, I know he likes me as a person and I know I love him as a friend, we've literally vowed to always be there for each other...and it's really hard to separate romantic passion (or the lack thereof) out from that. So, when a guy hasn't made a romantic gesture for 12 years, it's hard to be anything but pessimistic that he's interested, but...I still think that I'M interested, and I haven't communicated that to him, so what do I do with THAT?

And then there's the issue of us living very far apart and being at an age where we're more settled down. I'm not as concerned about that, though, because I feel like if the emotions work than we can figure the practicalities out, they're not THAT complicated.

So, in practical terms: Should I go visit him? Should I even make a move? Or should I just shrug my shoulders, try to stop fantasizing, and double down on the practicalities of my own little life?

My friends say, "maybe the time will never be right between the two of you." They've kind of written off the idea of us getting together as "oh, this will never happen, because you've been talking about crushing on him for so long (years and years) and it never has." Which might be right. But what if it's not?

I am scared of damaging our friendship. I don't want to be rejected. What if I make a move and he IS interested and then we find out that we aren't romantically compatible? Like, we kiss and it's terrible? I went to visit him a couple years ago with the plan to make a move during the week I was staying there but then I didn't, and he didn't, and...we never kissed or anything. In other words, I have all the usual fears.

But I just *like* him so much. He's so fun and funny and cool. I was reading an email from him this morning and he was just himself in it, I was having as much fun reading it as always, and it made me miss him so much that I was hit by a wave of...grief, I guess. Missing him and wishing I could be spending time with him, and just feeling...sad. And that's what brought this question on.

I'm sorry for such a mess of a question!

TLDR: I don't want to be stuck in the same old holding pattern as always, crushing on him but not doing anything about it, missing him but rarely seeing him, etc. But I don't know how to get out of the holding pattern in a sensible and respectful way.
posted by nowadays to Human Relations (16 answers total) 6 users marked this as a favorite
If you're working on being more direct with your desires, this seems like a blindingly obvious opportunity to practice.
posted by shadygrove at 12:20 PM on November 10, 2019 [20 favorites]

With the caveat that listening people in the internet with limited information can be a bad idea, I'd say it's entirely your move now. He made a romantic gesture, you rejected him. . . that he hasn't tried again and has remained a close friend isn't a sign that he isn't interested. (Sharing a bed *after* that seems just on the edge of cruel taunting on your part. . . but, perhaps it made sense in context.) It's a sign that he's a decent human being. And, it's a very good sign that he won't be offended if you ask him out and he says no for some reason. The ball is in your court, and it has been for 12 years.

Asking someone, "would you like to go on a date with me," is a magical strategy. It's the hardest thing in the world to say, but it always leads to a definite outcome and fewer regrets than leaving things ambiguous. There's a small chance it will change your friendship. . . but, you've already been through that once and it didn't happen last time. He might say no, probably for reasons that have nothing to do with you as an individual. But, if he's as good a friend as you think he is, he won't be offended or unkind.

Dating your best friend is awesome. Even if they live thousands of miles away. Even if they're bad at kissing. (That can be fixed.)
posted by eotvos at 12:30 PM on November 10, 2019 [14 favorites]

Here's a thought experiment: If he felt exactly the same way about you as you feel about him, and acted upon his feelings in exactly the same way that you do, how would you know? I don't think you would. You're not giving him any actionable information.

You need to communicate, explicitly, in whatever medium makes you feel most comfortable. Yes, you'll be making yourself vulnerable, and that's hard. And yes, you may be rejected, and only you know how capable you'd be of dealing with that. But to my mind, the only thing sadder than a person expressing their affections and being rebuffed is two people with a mutual attraction that neither of them knows about because neither of them has taken the risk of saying something.
posted by Faint of Butt at 12:30 PM on November 10, 2019 [5 favorites]

If your friendship survived you rejecting him, it can survive him rejecting you. and if he could tolerate being told No, so can you. whether he would say yes or no is impossible to tell, but the fact he never made another move means nothing except that he is an exemplary human being who genuinely respects the finality of a rejection, as everyone should. You are the one who most recently said No, so you are the only one who can open the subject again. A good friend wouldn't exhibit his attraction after he'd been turned down, so you can't figure this out by looking for signs.

he probably put away the idea of dating you a long time ago, so you will probably be better off thinking of this as a brand new idea you're proposing to him, and expect him to take a little time to react. he might even say No as a reflex and come back with a Maybe after thinking about it for a bit, same as you have. so tell him, but give it a little time to settle. and then if he does say No, you have to be just as good a friend to him as he's been to you for the last 12 years.

if you're not going to get to be with him, you'll be much better off knowing that for sure. you don't want possibility hanging over you and interfering with any other relationships you might have.

there's nothing impractical about this. it's not a sure thing, but it never is.
posted by queenofbithynia at 12:35 PM on November 10, 2019 [19 favorites]

I would go visit him for a short stay (like 2-3 days). Use the first couple days to gauge whether your interest in him is real and based on being with him in person, or whether it’s about being at a place in your life where you’re reflecting on past choices, questioning roads not taken, etc. If you confirm there’s something real there, have a talk with him on the last day of your stay about it and just be yourself and be honest—like “our friendship is really important to me and I would never want to do anything to hurt it, but sometimes I have this itch, like I wonder about what it would be like if we tried dating and being more than you ever think about that? Is it something you think we could try without messing with our friendship?” If he rules it out, then you are leaving shortly and won’t have to spend another night around. If he’s interested, you can talk about the future.

Keep it light. I would not confess love or put pressure on it or even bring up his interest in you at age 21, more that you think you both have chemistry and potential in the now.

I will say, for a while I had a friend who made me think “huh, maybe he and I would be good together...” when I was not around him, and every time I was around him, I went “oh yeah I have no romantic interest in him.” My musing about being with him was more about me and where my life was than about him as a person.
posted by sallybrown at 12:41 PM on November 10, 2019 [11 favorites]

Also, if you both say you’re really interested in each other, the chances of you kissing and you thinking “that was bad” are pretty small, because even if it’s sloppy and terrible it will still be thrilling in its own way.
posted by sallybrown at 12:43 PM on November 10, 2019 [2 favorites]

Contact him right away. Say, “I have a crush on you.” See what happens!

You might get rejected turned down, and that would suck for a little while. It sounds like you’re not going to lose him as a friend, though.

Don’t wait until you actually go see him; that would just make your visit more awkward. You can still visit if he says no (if you want to), but this way you have a bit of time to get yourself together.
posted by danielparks at 3:51 PM on November 10, 2019 [1 favorite]

I'm a big believer in being honest with good people. If someone is new in your life and your don't know, truly, if they can be trusted not to be a jerk, cruel, freaked out, then be circumspect. But if you know someone well enough in the ways you've described, I'd honestly say that you should take the chance. Yes, if he rejects you outright, you'll have to let go of the hopes and dreams. But you can't put all the pressure (and expenses) on a trip.

I don't know you, but I'd send him an email with a link to this AskMe and say, "Yeah, this is a tough situation. What would YOU advise the person asking the question?" and then wait. While it's obvious to both of you that it's about both of you, it gives some rhetorical cover. You lay all the messiness on the plate at once and then he gets to decide whether he wants to pretend (for both your feelings) that it's about random strangers. Then he can say it's not going to happen (maybe he'll say, "Yeah, the dude has moved on, but really values her as a friend) or that it could (maybe he'll say, "Oh, she should totally visit him!). Or maybe he won't resort to pretense at all, and he'll be honest. But unless you do something, you could be exactly where you are in another twelve years, and your life is too valuable for that.

It's not go or don't go, it's be honest, and then see where you are. But I wouldn't go until you have broached the subject and gotten some kind of answer, even if that answer is, "Whoa, I have no idea idea!"
posted by The Wrong Kind of Cheese at 4:20 PM on November 10, 2019 [1 favorite]

Nothing you've said here screams "not interested" and I think you should take your shot.

If it were me, I'd have the discussion first before booking a trip because it would feel unfair to show up and drop my crush on him and force him to come up with an answer on the spot with me in his living space. But I'm someone who likes a lot of space and time to process emotional things and my loved ones tend to be the same. Maybe your personalities and dynamics are different. Ask your question in whatever way makes sense for your friendship and history. But do ask it.

Good luck!
posted by Stacey at 6:30 PM on November 10, 2019 [4 favorites]

Contact him right away. Say, “I have a crush on you.” See what happens

YES! If you need extra help in making that scary statement then please imagine us mefites from this thread, in cheerleader clothes, standing around you, cheering you on as you get ready to say it, or press send. We're in AskMe colours, which look a bit weird in a cheerleading uniform context, but we have pom poms and are chanting TELL HIM! TELL HIM!
posted by greenish at 3:45 AM on November 11, 2019 [5 favorites]

OK, I'm going on the visit and will ask him out on a date once I'm there. Just a good, old-fashioned, "can I take you out on a date?" and if he says yes, then dinner/drinks/show.

Well, dinner/drinks/show regardless probably. But you know what I mean.

It would be gentlest to ask him out before I get into town, but I want to do it in person. Text or email doesn't seem right. I want to see his face and for him to see mine.

I'm extremely (extreeeeeeeemely) nervous, and keep thinking of reasons why this is a terrible idea. They all boil down to me being afraid of rejection.

posted by nowadays at 9:04 AM on November 19, 2019 [3 favorites]

Wishing you all the good luck with this. And good for you for sucking it up and saying something.
posted by jenfullmoon at 4:03 PM on November 19, 2019

Thank you all! We're together. We've been together since I made the trip. Everything is peaches and cream. When I've told old friends, they immediately interrupt me to say some variation of "finally!" and how much they love him and how they always knew we'd end up together. I really appreciate you all encouraging me because I don't know if I would ever have said anything otherwise. Thanks for giving me the courage.
posted by nowadays at 11:54 AM on February 5 [7 favorites]


Would you be interested in providing details about how it came about? ;)

So happy someone's got a happy story!
posted by jenfullmoon at 12:36 PM on February 5

Your update is the reason I read Metafilter!
posted by MountainDaisy at 9:26 AM on February 12

Awwww yesssssss!!
posted by sallybrown at 9:33 AM on February 12

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