We dated. I still like her. She...maybe still likes me. Now what?
September 25, 2019 1:15 AM   Subscribe

I feel kind of silly for even asking this question—it feels like I'm back in high school and bellyaching about dating all over again—but given that she (27) and I (31) are both kinda awkward and Not Good At Talking About Feelings, I don't know how to read this whole situation or how to calibrate my expectations or where to go from here. The gist: we dated, then un-dated two years ago, a bunch of things happened, but we've kept in touch all the while. I still like her, and feel like she *might* still like me, but I don't know how we'd move things forward given our current circumstances. More inside!

We met online a little over two years ago, and our first date was absolutely amazing—one of the best first dates I've ever had in terms of chemistry. I even blurted out to my friend the next day that I had met the person I was going to marry—that's how strong that feeling was. I found out on our second date she was taking a year off at home, after having finished her third year of med school, to help take care of her dad with cancer, which cut into her free time quite a bit, considering that she's (like myself) an only child, but I was totally OK with it. We continued to date casually for a couple more months, until she broke things off all of a sudden, saying that she wasn't ready to be in a relationship with everything going on. It sucked a lot to be on the receiving end of that, but I understood where she was coming from and we ended things on what felt like good terms, and I got the impression was that the door was open—if ever so slightly—to perhaps trying again further down the road.

Her dad ended up passing about five months later, and a month after that, she went back to school—about a five-hour drive away—for her last year and to go through the residency matching process in the fall and winter. I can't imagine how incredibly stressful that whole time must have been for her, but we checked in intermittently throughout, over text, and she kept me updated as she matched into her top choice of program—an extremely well-regarded academic program in a competitive specialty—in the same location, at which she's now in her first year of training. I was, and am still, really proud of her, and incredibly impressed by what she had been able to achieve despite the circumstances.

We've still been talking, and while I tried to give her space during her fourth year, given that she was in the thick of residency application and interview season, and that I was still trying to figure out what direction to take my PhD in—not to mention that I dated other people in the meantime, which led to me falling out of contact a bit—it feels like she's put a lot of effort into staying in touch and keeping our texting going all this time. Perhaps quite a bit more effort than I have, it seems like—she once sent me thirty texts with pictures and stories from a vacation she took, not to mention countless (endearing!) double texts from her. The topic of either of us dating or spending time with other people never comes up—not once in these past two years. And I don't know what to make of it—out of the dozen or so people I've dated and then un-dated over the last five years, I've never kept in touch with any one of them anywhere close to the extent that she and I have. I have to admit that a part of me had resigned myself to moving on from any hopes of getting back together, given the distance, and the impracticality of keeping a relationship going with someone about to undergo residency training.

But an even bigger part of me has always wondered about the "what if?"—what if we could make something work?—and while that's waxed and waned to some extent over the last two years, those feelings have have ramped up recently, even as she's graduated and started residency. We ended up meeting for coffee back in May, when she was back in town visiting family right before heading back down for graduation, and ended up hanging out for three hours and walking around the city. When I got home, I saw that she had texted me how good it was to see me, that she had missed me, and that it "reminded her of old times". Yay! But then again, she's starting residency soon. Oh well. She told me to let her know when I'd be coming back to her city, and we keep texting off and on, even as she begins residency and starts working 90-100 hour weeks. Three months later, I tell her that I'm finally going to be making the drive down, and she seems excited and says that she can't wait to see me. I did my undergrad in this city, and while I still have many friends there, I have to admit that a big reason for my visit was so that I could see her.

We don't text for a week or two, and I'm like, OK, she's on a really shitty rotation right now, so if she texts, great. If not, that's OK too. I make the drive down, and that night, on the same day I told her I'd be down, I get a text seemingly out of nowhere from her welcoming me back to her city and asking if I made it down okay. Yay, she remembered! We make plans for dinner the night following her "easy" day—a day where she still has to work 14 hours, and the night before a 28-hour shift starting the next day. We get dinner, and it is nice (even though it's just dinner—a 3-hour dinner), and I feel myself starting to feel the damn butterflies all over again. Same "I-missed-yous", same allusions to old times. That was about a week ago now. We're still talking, and I still feel the butterflies. But I don't really know where to go from here.

That said, I feel like it's important to reiterate that we're both kinda awkward as all get out and aren't really that great about talking about our feelings, nor about serious-ish stuff—in fact, I wished she'd have opened up more, when we were dating, about what she had been going through, but I fully understood that that was her choice and didn't press her on that. If not for those two factors, I feel like we'd have long since been able to clarify just where exactly we both stand and how we feel about each other. Then again, she's in residency and working her butt off all the time, and we live quite a ways apart, so, realistically, it doesn't seem like we can bring up the idea of restarting things any time soon. Like I said earlier, I feel like we could make something work—given that I have so many ties to her current city, and I've reached the stage of my PhD where I'm done with my classes and I can do my research from basically anywhere, since I'm not tied down to a lab—if not now, then maybe next year, when she's got intern year behind her. I've got nearly two more years to go in my PhD, and her, nearly four more years of residency (hers is four years total).

So—where do I go from here? Do I just play along and stay in touch until she's hopefully in a better place—perhaps next year—to think about getting back together? I'm not opposed to the idea of a semi-long-distance relationship (given the flexibility that I have right now), and I've done it in the past, so I know what I'd be in for, but I have absolutely no idea how I'd even bring that up under these circumstances. I think she's amazing, but I also fully understand the reality here—so I'm not completely hung up on her and I'm not ruling out dating other people in the meantime, but, damn, it'd suck to pass on the possibility of what things could be between us. Have you ever been in a situation like mine before and managed to find some resolution out of it? If so, I'd really love to know...
posted by anonymous to Human Relations (16 answers total) 2 users marked this as a favorite
both kinda awkward and Not Good At Talking About Feelings

You two need to have an awkward and not particularly aesthetically pleasing talk about your feelings or lack thereof.

If you are eventually going to be together you’re going to have to learn how to do this anyway, so consider it staying ahead of the curve.
posted by Tell Me No Lies at 1:27 AM on September 25, 2019 [13 favorites]

I think what you told us here is what you should be telling her.
posted by nat at 1:43 AM on September 25, 2019 [4 favorites]

A friend of mine recently got a message from a friend of hers that was basically like:

"Our friendship is amazing, and I'd be super happy if it stayed like it is. But I'm really into you, and I wonder a lot if you're into me too. If you're not, I'll totally just go back to enjoying our friendship for its own sake, and I promise I won't be hurt or awkward about it or keep bringing it up. But if you do think you'd like this to be something more, I'd love to know."

She wasn't at all interested, and said "no, sorry" pretty much immediately. But she was so blown away by the kindness of the message itself that it actually made her feel more comfortable with the friendship, not less, despite their different levels of interest.

Anyway, I thought I'd share that summary because it seems to me like a pretty ideal way to raise the subject. Add a sentence about "I'm worried a long distance relationship would be hard, but I think we could make it work if you were interested, so let's talk about that" and I think it could be the right conversation-starter for you.
posted by nebulawindphone at 4:16 AM on September 25, 2019 [28 favorites]

But yeah, say something now. I've often wished I'd spoken up about feelings sooner. I've never wished I'd waited longer.
posted by nebulawindphone at 4:19 AM on September 25, 2019 [9 favorites]

I think it's fine to ask directly (but thoughtfully, like some of the suggestions above) about this.
posted by needs more cowbell at 4:50 AM on September 25, 2019

Having been with my spouse during her medical residency, that's about as "dating" as it gets, well, besides sex. If this is what you want and you want to name it, let her know. Also let her know what your expectations are, even if that's "I want to be as flexible as possible to allow you the time and space to be fully engaged in residency." Use your words.

Most of the spare time we had in residency was a "stolen" hour here and there, so being in the same city where spur of the moment seems more possible will greatly increase the time you can spend together. Plans are really hard because you feel the pressure to get stuff done before that and the guilt of not working. You also feel pressured to feel like it's the most fun ever to be worth it. That said, there are definitely going to be blocks of easier rotations or ones that suit themselves to having a relaxed dinner ever night. Maybe your happiness lies there.
posted by advicepig at 6:39 AM on September 25, 2019 [1 favorite]

"I still feel butterflies when I see you, and the only reason I haven't broached the subject is out of respect for how busy you are with your residency. Rather than making guesses, I'm just going to ask: Do you think there's a way forward for us to date again?"
posted by vitabellosi at 7:33 AM on September 25, 2019 [11 favorites]

^ This. But I would also add that if you are prepared to make it work around her residency, to be available for stolen hours and are ok for her schedule to dictate your relationship, make this clear. Because I can guarantee you if she is keen, this will be what’s holding her back and she’ll need to know that you get it and still want to move forward and won’t resent her job (in as much as you can know this.) But have the conversation and let us know how it goes!
posted by Jubey at 9:20 AM on September 25, 2019 [2 favorites]

"I also fully understand the reality here—so I'm not completely hung up on her"

Hmmm, you seem extremely hung up on her, to be honest!
There is literally nothing you can do in this case but tell her how you feel. I sometimes think that the usual advice to always be very explicitly "I am romantically interested and want to go on a date" is a bit unromantic and pushy, but in this case it seems totally appropriate. The risks: she has already broken up with you before and hasn't mentioned getting back together, and she doesn't seem to have any time for a relationship. On the other hand, she makes it a priority to stay in regular touch with you and took a lot of initiative in getting together when you were in town.

I think this is worth using your words! You are daydreaming about moving to her city and starting a life together. Find out if she's thinking about the same things.
posted by cakelite at 9:34 AM on September 25, 2019 [1 favorite]

So, I kind of think she's stringing you along. I think that if she were really into you, she would have kept dating you years ago, but she likes you enough to keep in touch, and you are giving her something -- positive attention, friendship, etc -- to keep around. The fact that she doesn't talk about anyone else she might be dating also contributes to my thinking on this. That's my hunch.

I also think that your lingering crush is likely going to keep you attentive to her and possibly prevent you from fully diving in with anyone else. That you don't tell her about your other dates aligns with this.

So I think that you should look to resolve this one way or another -- because then you'll either be dating her or know that it's not an option on the table, and you can then move on and find a relationship (because it seems like you want one).

So, yeah, have this conversation with her. "Hey, I really think you are amazing. Is there any chance of us dating again?"

If the answer is no, I think it might be good for you, if still feel hung up on her, to let this friendship go a bit. As it is now, you are projecting a lot of fantasies onto what it would be like to date her, and fantasies like that can keep us from moving on. If she says no, and you all do want to continue being friends, then you probably need to be able to talk about other people you are dating. If I were dating someone in any kind of serious way and that person was in regular contact with an ex who didn't know anything about me -- that would be a huge red flag that that relationship wasn't actually resolved.

Good luck either way!
posted by bluedaisy at 11:43 AM on September 25, 2019 [3 favorites]

If you need another reason besides the potential future awesomeness of a relationship and to avoid wasting your precious life waiting for someone (if she isn't interested), another reason to resolve this is that you don't want to be one of those friend zone people who hangs around someone pretending just to be friends even though that's actually not an emotional option for you -- it's kind of creepy, shows disrespect for both of you, and is not sustainable. I'm not saying you're being creepy now, just suggesting you think of the creepiest friend zone examples you can come up with and use "that's not me!" as motivation. (Also, I say all this as someone who totally got "friend zoned" and did that whole hanging-on thing, so I'm not judging anyone.)
posted by salvia at 1:08 PM on September 25, 2019 [1 favorite]

I also wanted to add that although I said she's stringing you along, I don't mean to suggest she's doing this consciously, in a cruel or mean way. I mean that I suspect she knows you like her and might be interested in dating and ignores that because she's getting some value from that.
posted by bluedaisy at 1:21 PM on September 25, 2019 [1 favorite]

the topic of either of us dating or spending time with other people never comes up—not once in these past two years. And I don't know what to make of it

Maybe she hasn't dated other people?

Ok, reality check: She already did date you, and she ended it. She said it was because of everything going on in her life at the time, but how do you know it was *only* that? Now that she has a whole bunch of other stuff going on in her life, you think she'd be available for a relationship again? All her actions after you broke up that you described here can be seen as her expressing friendship for you, and I get that you're crushing on her and may not be really able to see that.

she's in residency and working her butt off all the time, and we live quite a ways apart, so, realistically, it doesn't seem like we can bring up the idea of restarting things any time soon. Like I said earlier, I feel like we could make something work

Even if you were to bring up the idea, how realistic is it that you could actually have a relationship what with her high-pressure schedule AND the distance (and if she wanted it)? The way you're thinking about how a relationship would logistically work is a little presumptuous/very cart before the horse. You're not really thinking enough about whether she WANTS to date you (again); you're just making excuses for why you guys haven't talked about it (i.e. because you're awkward etc.).

Given all that (and have a read of this Dr. Nerdlove post, he tells the OP that the woman he's crushing on is expressing friendship, nothing more, so I think you can learn something from that), I think you should go with nebulawindphone's brilliant script and see what happens. Who knows, if she reciprocates, I'll eat my hat.
posted by foxjacket at 2:41 PM on September 25, 2019

I think she does like you, but maybe not enough to try to juggle you and the complications of life? Like I really want to root for you and I think she likes you back and I definitely have that vibe from reading this, but you still have huge complications on her end still going on for years that will probably mean she still can't or won't feel like she can manage to date you, and long distance, no less. That said, this is giving me "beyond just friends" vibe reading it all, so "maybe someday" could happen.

What gives me hope is your saying that you may have some flexibility to move with regards to your program. If you have other ties to her city and it wouldn't be just moving only to be with her (what advicepig said is what i'm thinking of here, it'd be easier to have a stolen hour that way), I think it's fair to say what everyone else here said, but maybe throw in that you understand she doesn't have much free time and the long distance and all, but that you might consider moving closer to her in the future and see how that goes. Even I feel like it's a little presumptuous to say this and I'm not sure if it's correct, but I also kinda feel reading this whole thread that it might help.
posted by jenfullmoon at 6:52 PM on September 25, 2019 [2 favorites]

Would you be willing to move to the city of her residency if she were interested in resuming a relationship with you? Or, in your daydreams about her, are you imagining that once she completes four years of residency she would look for a job where you are? It might sound crazy to be asking yourself that question at this stage, but you should consider it, especially because she sounds like someone who is very career focused. Maybe she reciprocates the feelings, but knows herself well enough to know she doesn't have the (considerable) mental and emotional bandwidth necessary to sustain a long distance relationship.
posted by BusyBusyBusy at 11:23 AM on September 26, 2019

I feel like sex is the elephant in the room here.

You two used to date (and presumably have had good sex?) and I can’t tell from reading this, but when you last saw her, were you sexually intimate at all? Was there any reciprocated sexual banter, or tension? Shooting from the hip here, but if she didn’t signal any sexual interest with words or touch, or try to be with you, or even flirt with you, and you’d been together before and know her signals? I’d probably give up on rekindling this, and let it be.

As a cishet lady, I feel like the times I have been in her shoes — ambivalent, kind of wanting the idea of a more formal relationship with a particular man, but that being utterly outweighed by the challenging realities of being in a life/career situation where I felt like the time/distance/amount of coordination and planning that would have been required were just not worth it, and would have preferred someone local.

If you guys had fallen passionately into sexytimes together, and she really missed you, I’d be more inclined to see this as her wanting more from you. As such, I’m concurring with the “she’s stringing you along, but not maliciously” crew here.
posted by edithkeeler at 2:59 AM on September 27, 2019

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