Reconnecting With Someone

[MusicNerd]

Hi, hope y’all are doing well! I’m planning on reaching out to someone I briefly dated soon, but now I’m starting to second-guess myself and could use some advice.

A couple months ago, I was dating someone for about a month and we really hit it off— we had great communication, they were super great about respecting boundaries, and I felt like I could fully be myself around them. I really appreciated how we could be so open and vulnerable with each other and create that kind of space together. On our second-to-last date, they even brought up the “what are you looking for in a relationship?” talk, and we realized we were looking for the same things and wanted to keep seeing each other.

A week after that, they realized that their professional life was in flux and that they would be too stressed to start a new relationship for the next few months while they sorted that out, so they ended things at the end of our last date. (Sidenote: I understand where they were coming from, but it did not feel great to find that out at the end of a date, since it felt like they were acting like everything was fine for several hours before letting me know their thoughts— I know they likely didn’t intend for that to be hurtful, and I let them know how I appreciated their honesty, but I definitely would’ve preferred knowing how they felt before we spent the day together.)

They offered to be friends, and I let them know I’d think about it, because: 1. I was surprised and hurt and needed to process things, 2. I’ve experienced being strung along by people in the past and was wary of experiencing that again, and 3. I didn’t know how I’d feel about being friends if they started seeing someone else, for instance. Basically, I had things to consider, and I didn’t wanna fall back on my people-pleasing tendencies, so it had nothing to do with them as a person. (I didn’t express these reasons to them, I just let them know I’d think about being friends and we ended things on a nice note.)

Then, less than a week after our last conversation, A LOT of things in my life hit the fan and I had to focus on taking care of all of that. Ironically enough, given all that suddenly cropped up in my life, I likely would’ve asked them to take a break from dating each other not long after they asked that of me. (Good timing, I guess?)

Now that a couple months have gone by, and things on my end have started to settle down, I’ve been thinking about reaching out to them to see how they’re doing. I’m also wondering if maybe things in their professional life have settled down a bit and how they’d feel about reconnecting.

Frankly, I miss them. They’re a really great person and I’ve thought a lot about them ever since we last spoke. I’d ideally like to try dating each other again, if things have settled down for them, but I’d also respect being friends if that’s what they would prefer. My message I’m planning on sending them is just a brief check-in to see how they’re doing and letting them know I’m thinking of them, but I’m wondering: If we were to meet up, would it be a bad idea for me to bring up the idea of potentially dating each other again, while also expressing being open to friendship? Would it come off as rude or selfish to bring that up, or am I just overthinking things out of fear? Any input is appreciated, thanks!

Summary: Dated someone briefly, life circumstances made it hard for us to date at the time, I’m planning on reaching out to them soon (now that it’s been a couple months) to either try dating again and/or being friends. Is it a bad idea for me to bring up the idea of potentially dating each other again?

[Emily N]

Hi MusicNerd,

Ahh it feels so good to have connections like the one you’re describing! It’s understandable that you didn’t feel great about how things ended with this person, and I’m glad you were able to communicate these feelings to them. It’s also really important and admirable that you took time to actually think about whether being friends, rather than dating, is what would actually be best for you. It can seem like a default to accept friendship because we want to spend time with people we have feelings for, but it’s true that there are many things to consider.

If you reach out to them again, make sure you have a clear idea of what outcomes would feel good to you and which ones would not. At the end of your post, you mentioned that you were open to friendship – does this feel like a good outcome for you? It sounds like you are interested in dating again, and and I think it’s reasonable to let them know this. If they are open to meeting up, you could see how it feels while spending time with them to gauge whether you want to bring this conversation up in the same day or the next hang out. It sounds like you were both thoughtful in your communications together before, and part of communicating well with each other is being open about your needs/desires out of the relationship. How does this sound?

[MusicNerd]

Hi MusicNerd,

Ahh it feels so good to have connections like the one you’re describing! It’s understandable that you didn’t feel great about how things ended with this person, and I’m glad you were able to communicate these feelings to them. It’s also really important and admirable that you took time to actually think about whether being friends, rather than dating, is what would actually be best for you. It can seem like a default to accept friendship because we want to spend time with people we have feelings for, but it’s true that there are many things to consider.

Hi Emily N, thanks for responding! Yeah, our connection did feel really great, to be honest. It definitely felt like there was something special there.

Also, I expressed how I appreciated them letting me know how they felt, but I didn’t express to them why I wasn’t okay with how things ended… but maybe I should at some point? I’m not sure. But yeah, I didn’t think about taking time to think things over as an admirable thing, but thanks for pointing that out!

If you reach out to them again, make sure you have a clear idea of what outcomes would feel good to you and which ones would not. At the end of your post, you mentioned that you were open to friendship – does this feel like a good outcome for you? It sounds like you are interested in dating again, and and I think it’s reasonable to let them know this. If they are open to meeting up, you could see how it feels while spending time with them to gauge whether you want to bring this conversation up in the same day or the next hang out. It sounds like you were both thoughtful in your communications together before, and part of communicating well with each other is being open about your needs/desires out of the relationship. How does this sound?

In terms of whether or not friendship would feel good, I think honestly it would feel a bit weird for me at first. But I also think that if it didn’t feel good for me, I’d let them know if I needed space. So, yes, dating would feel like a better outcome for me, but I’d also want to be respectful of what they want too.

Also, I’m glad it doesn’t seem unreasonable to bring up dating again. I have no idea how I’d bring that up though, it seems pretty nerve-wracking! I guess I’m afraid of how they’d react to me bringing this up to them, or possibly a fear of them rejecting the idea, so maybe that’s part of my nervousness.

[Emily N]

Also, I expressed how I appreciated them letting me know how they felt, but I didn’t express to them why I wasn’t okay with how things ended… but maybe I should at some point? I’m not sure.

Oh gotcha! If you don't think it's helpful to share, you aren’t obligated to express your feelings with how things ended, either! If it feels relevant to bring up in the future, you can do that too It sounds like you have a strong idea of what you want and how to communicate that with them, that’s great! I can understand how it would be nerve-wracking to bring up dating with them. Does it make sense for you to bring it up at the end of the hangout or the second hangout, or would it feel better for you to bring it up at the beginning? It’s possible that the conversation will come up naturally if you both hang out again.

Rejection is a painful experience for sure. But no matter what the outcome is, it also sounds like they have been kind and thoughtful with you in your past experiences, which will hopefully carry over into the future. And you can’t know what they are thinking unless you ask them I suppose!

[MusicNerd]

Also, I expressed how I appreciated them letting me know how they felt, but I didn’t express to them why I wasn’t okay with how things ended… but maybe I should at some point? I’m not sure.

Oh gotcha! If you don't think it's helpful to share, you aren’t obligated to express your feelings with how things ended, either! If it feels relevant to bring up in the future, you can do that too It sounds like you have a strong idea of what you want and how to communicate that with them, that’s great! I can understand how it would be nerve-wracking to bring up dating with them. Does it make sense for you to bring it up at the end of the hangout or the second hangout, or would it feel better for you to bring it up at the beginning? It’s possible that the conversation will come up naturally if you both hang out again.

Yeah, I think I’d let them know how I felt about the way things ended if it came up in some way in the future. And I’m not sure yet when I’d wanna bring up dating to them. Maybe I could talk over with my therapist how/when I’d wanna go about bringing that up. I think I’d wait for it to naturally come up if we were to meet up again, but who knows.

Rejection is a painful experience for sure. But no matter what the outcome is, it also sounds like they have been kind and thoughtful with you in your past experiences, which will hopefully carry over into the future. And you can’t know what they are thinking unless you ask them I suppose!

That is a good point! I have no idea what they’re thinking or feeling anyway, so there really is no other way of knowing unless I talk with them (I wish there was a less vulnerable way of finding these things out lol).

[Emily N]

That sounds like a good plan, talking about it with your therapist could be really helpful! It’s okay (probably even helpful) to start slowly with reconnecting with them to get a sense of where you both are first. You don’t have to jump into the hardest conversation!

(I wish there was a less vulnerable way of finding these things out lol).

So relatable... being vulnerable is hard! But at least it can also be rewarding

[MusicNerd]

That sounds like a good plan, talking about it with your therapist could be really helpful! It’s okay (probably even helpful) to start slowly with reconnecting with them to get a sense of where you both are first. You don’t have to jump into the hardest conversation!

Yeah, that sounds like a good idea. Jumping right into it sounds pretty nerve-wracking and I’d rather not do that lol

(I wish there was a less vulnerable way of finding these things out lol).

So relatable... being vulnerable is hard! But at least it can also be rewarding

That is also very true! I know that if I didn’t bring this up to them, I’d likely be stuck with “what if?” which makes me think asking them about it might be the move.

Thanks for taking the time to talk this through with me! I’ll let you know how it all goes.

[MusicNerd]

UPDATE: I reached out to them today and they admitted to thinking of me too! I wasn’t sure how they’d feel about hearing from me, or if they thought about me much, but I guess they were glad to hear from me. We had a nice texting conversation and we’re gonna be meeting up next weekend. I’m definitely nervous, but I’ll be meeting with my therapist a couple days before I see them, which will be helpful. But yeah, I’ll keep you posted on how this goes!

[Elise]

Glad to hear that things are going in a positive direction for you, and timing this in a way that works well with your therapy sessions sounds like a good idea. Yes, do let us know how you go

[MusicNerd]

So, we met up today and it was nice! Pretty light-hearted conversation, no talk of dating or anything— just a generally nice catch-up. My goal for today was to stay present and have a good time, which I feel like I did! I can give myself a pat on the back for that lol

Not sure if we’ll meet up again or anything; they said we should do this again though, so who knows!

[Sam W]

Hi MusicNerd,

Hooray, I'm so glad it went well!

[MusicNerd]

Thanks, Sam! We’re likely gonna be hanging out again sometime next week, and while I’m looking forward to seeing them, I’m also still not sure about how they feel— they could potentially feel too busy to date, or maybe they’ve lost interest in me in that way, or any number of things.

I’m nervous about talking with them about this, but I also don’t know if I’ll bring it up next time we meet. I don’t even know how I would bring it up, you know? Sorry, I feel silly being worried about this kind of thing.

[Elise]

Hi MusicNerd, glad to hear that you had a good time hanging out with this person, and will get to again

It is totally natural to be nervous about asking this kind of thing, as it is a bit of a vulnerable thing to put yourself out there, but is the best way to get a clear answer and know where your friendship/relationship is at the moment. Practicing asking in a really clear way can be a good way to prepare for this kind of situation. How would you feel about saying something along the lines of "How are you feeling about dating now that things are a bit calmer for you professionally? (or more accurate words to their situation here)", I'd like to try dating again with you if you'd like to, too?". It can also be good to think about how you might respond if the conversation doesn't go how you'd hope, if dating is still not something they have the bandwidth perhaps to do, or isn't something they want to do at the moment.

This article by one of our fellow volunteers, Mo, goes into more detail, and also contains some great further articles at the bottom, including one about handling to a 'no', if that is what comes to pass. How do you think you'd feel if they say yes, or if they say they'd prefer to be friends?

[MusicNerd]

Hi Elise, thanks for responding! If they were to express not wanting to date, I would definitely respect that. I’d have to think about how I would express that, because I’m not trying to convince someone to date me, you know? Not very romantic lol

If they expressed just wanting to be friends, I would be a bit bummed (internally, like I wouldn’t tell them that and make them feel bad) and it would feel a bit weird for me at first, but ultimately I’d be okay. It would feel better to know where I stand than to just continually be stuck in a state of questioning.

And I like the way you posed the question about asking how they feel about dating in general given how their professional life has been going, since it takes the focus off of me and makes me feel less anxious in that sense. Also, I’ll check out the article Mo wrote too!

[MusicNerd]

Update: We were supposed to meet up tomorrow, but they had to cancel due to being busy (which is fine, because life happens). They asked to reschedule, but I’m thinking they’ve lost interest or might be too busy to date and I should quit while I’m ahead (a.k.a. not pursue dating them or bringing that conversation up).

It could just be a one-off thing, or it could be a sign to abandon ship. Not sure what to do or how to feel at this point, but all I know is I’m getting the urge to run away now, which isn’t a fun feeling.

[Sam W]

Hi MusicNerd,

If this is a one-off for them and they're usually pretty good about plans, then I would try not to read too much into it; this time of year in particular is busy for a lot of people. However, if this is a pattern with them, that could be telling you something about their scheduling habits in general or about their interest in seeing you.

You mention that urge to run; where do you think that's coming from?

[MusicNerd]

Hi MusicNerd,

If this is a one-off for them and they're usually pretty good about plans, then I would try not to read too much into it; this time of year in particular is busy for a lot of people. However, if this is a pattern with them, that could be telling you something about their scheduling habits in general or about their interest in seeing you.

Hi Sam! Yeah, tbh this is the first time they’ve ever asked to reschedule something with me, so maybe I’ll just give it a few days to see if they reschedule. If not, then I’ll know where I stand in relation to their schedule or (lack of) interest.

You mention that urge to run; where do you think that's coming from?

Hmm… I guess fear? In the past, I’ve usually been the one to end things with people first in dating situations. But I guess sticking around to see what happens, instead of running away out of fear, makes me anxious since I know I could be setting myself up for rejection.

[Sam W]

I totally understand that feeling of fear. If you're someone who's prone to anxiety about relationships, it can be really tempting to try and get out ahead of rejection or disappoint by, essentially, taking yourself out of the situation. Sometimes that's a sound call, but often it can take us out of things before we fully get a chance to explore them and see what the outcome actually is.

[MusicNerd]

I totally understand that feeling of fear. If you're someone who's prone to anxiety about relationships, it can be really tempting to try and get out ahead of rejection or disappoint by, essentially, taking yourself out of the situation.

Yes, that’s exactly it! It’s like I’m beating people to the punch by leaving the situation first.

Sometimes that's a sound call, but often it can take us out of things before we fully get a chance to explore them and see what the outcome actually is.

Ugh, I hate that you’re right, but you’re right. lol It’s true, I don’t actually know how things will play out unless I stick around to find out.

My anxiety makes me think that I know what’s gonna happen, before it does; but as I’m writing this, I’m realizing that that’s probably a cognitive distortion coming in to play.

[Carly]

Hey MusicNerd -- you're totally right, and I think you're on the cusp of learning something really important about anxiety and how it plays out interpersonally. Sometimes our own overthinking makes us believe we do know what will happen, because we've quite possibly thought of every way it could. Often times it doesn't always include the scenario in which it works out, we get what we want, or we are braver than we expect.

With that said, I wanted to just say that using how and when they reschedule with you as a thermometer for their interest in you may not be the best way to approach it. It sounds like this person has a lot of stuff going on professionally, and sometimes that is beyond one's own control. Because of that, it may not reflect how they're feeling accurately, which in turn may give you a read of the situation that isn't accurate. Does that resonate with you at all?

[MusicNerd]

Hey MusicNerd -- you're totally right, and I think you're on the cusp of learning something really important about anxiety and how it plays out interpersonally. Sometimes our own overthinking makes us believe we do know what will happen, because we've quite possibly thought of every way it could. Often times it doesn't always include the scenario in which it works out, we get what we want, or we are braver than we expect.

Hi Carly! No, you’re totally right. You’d think after having anxiety (specifically OCD) my entire life I’d be able to notice this kind of thinking as soon as it happens— but alas, anxiety is sneaky like that sometimes!

With that said, I wanted to just say that using how and when they reschedule with you as a thermometer for their interest in you may not be the best way to approach it. It sounds like this person has a lot of stuff going on professionally, and sometimes that is beyond one's own control. Because of that, it may not reflect how they're feeling accurately, which in turn may give you a read of the situation that isn't accurate. Does that resonate with you at all?

Yeah, it definitely resonates. They actually messaged me today and apologized and explained how this week is particularly busy for them since they’re making a lot of big decisions. We rescheduled to meet this weekend, so it’ll be nice to see them.

Now my anxiety is telling me that they’ll be too busy to date and I shouldn’t pose that question to them because of this. But who knows, I’ll probably bring it up to my therapist this week to see what she thinks.

I’m realizing that I’m possibly deciding for this person what they are and aren’t able to handle right now by assuming their response, but perhaps that’s also a defense mechanism too. Not sure where that line is, and I don’t even know if what I’m saying makes any sense?

[Emily N]

“You’d think after having anxiety (specifically OCD) my entire life I’d be able to notice this kind of thinking as soon as it happens— but alas, anxiety is sneaky like that sometimes!”

Ohhh yeah, I also feel like I’m constantly learning something new about my mental health and how it plays a role in my life - it changes depending on what’s happening in my life at the time. I guess I appreciate that there are always new things to learn about myself

“I’m realizing that I’m possibly deciding for this person what they are and aren’t able to handle right now by assuming their response, but perhaps that’s also a defense mechanism too. Not sure where that line is, and I don’t even know if what I’m saying makes any sense?”

I’m so glad you took a few days and they reached out to you to reschedule. And yes, that makes sense! Sometimes when there is uncertainty, especially about emotional topics, it’s hard not to create our own narrative of what’s happening to make sense of things that are up in the air. But it also sounds like you are doing a good job grounding yourself and reminding yourself that you can’t really know their side of the story without having a conversation.

[MusicNerd]

Ohhh yeah, I also feel like I’m constantly learning something new about my mental health and how it plays a role in my life - it changes depending on what’s happening in my life at the time. I guess I appreciate that there are always new things to learn about myself

Wow, I really like that mindset! I guess I’m learning some new things about myself.

I’m so glad you took a few days and they reached out to you to reschedule. And yes, that makes sense! Sometimes when there is uncertainty, especially about emotional topics, it’s hard not to create our own narrative of what’s happening to make sense of things that are up in the air. But it also sounds like you are doing a good job grounding yourself and reminding yourself that you can’t really know their side of the story without having a conversation.

Tbh they didn’t even take a few days to reschedule— it was literally the next day… So, I was anxious over nothing (what a surprise! )

Yes, that’s exactly it! I’m totally creating stories to deal with uncertainty. And yeah, it’s definitely tough to keep myself grounded sometimes, but I’m trying to remind myself that I actually can’t read people’s minds or know what they are/aren’t able to handle.

Maybe they are too busy, or maybe they’re not, but either way I won’t know til I ask… which is annoying that I’ve gotta put myself out there like that, but oh well lol

[Sofi]

Hi MusicNerd, hope it's okay that I chime in! I love what Emily said and can relate to feeling like learning about my own mental health is actually productive. I'm so glad you see it that same way. As for the whole creating narratives as a coping mechanism, that is soo normal/common, you have no idea! It may feel annoying to have to put yourself out there just to get the answers you want, but I always try to think about the other person's perpective--perhaps they are also going through anxiety and similar things. When you think about the world like that, like everyone else might also be having anxiety, it helps you feel better about your current situation because it's no longer personal. It's also important to work on building some confidence to bring things up directly to people (such as asking if they're too busy for dating or not, etc--always respectfully and kindly, of course!) You're very self aware and are doing great by acknowledging your anxiety and defense mechanisms, so kudos on that

[MusicNerd]

Hi MusicNerd, hope it's okay that I chime in! I love what Emily said and can relate to feeling like learning about my own mental health is actually productive. I'm so glad you see it that same way. As for the whole creating narratives as a coping mechanism, that is soo normal/common, you have no idea! It may feel annoying to have to put yourself out there just to get the answers you want, but I always try to think about the other person's perpective--perhaps they are also going through anxiety and similar things. When you think about the world like that, like everyone else might also be having anxiety, it helps you feel better about your current situation because it's no longer personal.

Hi Sofi! Of course, it’s totally okay if you chime in. And honestly, that’s a very valid point - re: them feeling anxiety too.

I remember when we were first dating, we talked about all the times both of us thought the other person wasn’t interested, because of overthinking and anxiety— it was really eye-opening and kinda funny at the same time.

Also, they also seemed pretty nervous when we met up last time… So, you’re right— it’s very possible that the anxiety (over whatever it is they’re nervous about) isn’t just on my end, and that adds another layer I hadn’t considered.

It's also important to work on building some confidence to bring things up directly to people (such as asking if they're too busy for dating or not, etc--always respectfully and kindly, of course!) You're very self aware and are doing great by acknowledging your anxiety and defense mechanisms, so kudos on that

Yeah, building confidence around these kinds of situations is definitely tough, even when I know I’m going about it in a respectful way. And thanks for calling me self-aware! I really try to be, so that means a lot.