Advice about missing a chance with my crush, please

Hey everyone,

There is a man I use to work with who I really got along well with, had a ton in common with, and always harbored a crush on. (Kinda like a Jim and Pam friendship, for any office fans out there). He is 26 and I am 30. I've been working somewhere new for the past year and a half, but I ran into an old colleague who still works with him. As we were chatting she mentioned how much he still talks about me and how he says he kicks himself for not having the nerve to ask for my number before. I was happily surprised because I always found it hard to tell if he liked me more than a friend, but apparently he's "practically in love" with me (her words lol).

Long story short, for about 2 months we've been texting here and there - catching up, reminiscing, and playful joking but we never got into any real talk about feelings. I kinda felt like we were each waiting for the other to make a move and ask the other out. But I'm terribly shy and have never done this. I've been trying to work up the nerve and be direct about my feelings. Unfortunately, I found out he JUST (within the past week) got back together with his ex-gf, who he dated for about 6 months in 2017.

I'm pretty upset that I let this opportunity slip away. I am terrible at letting my feelings be known (super shy). I know I should have made a move when I had the chance... it was practically laid out there for me because I was TOLD he really liked me. I'm wondering if the fact I didn't lay my feelings out made him feel that I didn't reciprocate? He never told me himself how he felt, but I think he knows the colleague filled me in...

I feel like laying it out there for him, but it's so inappropriate now. I hate that I spent so much time trying to get a backbone that his ex slipped back into the picture before I could do anything. I have no idea how serious things are with them... I just know that she's 21 and they dated for a bit last year.

I'm not really sure what I'm looking for here, just terribly sad. I can't say anything now, but I can't help but wonder how different things would have been if I wasn't so scared.

Well, the good news for you is that this woman is 21 and they've broken up at least once before, so it's quite likely that they won't make it long-term. Perhaps next time he tries reaching out to you, you can tell him you think it would be more appropriate if he contacted you when/if things don't work out with the gf. That way you're backing off but also letting your interest be known. I think it's a better idea to back off when he's with her if friendship is not ultimately what you want, because otherwise you'll be hanging on and it will just be torture seeing him with her. Try to put your mental energy into your hobbies, friends, and work so that you are available for another dating opportunity should it present itself.

Thank you for your response. I agree that it may be difficult emotionally to be in touch when he's with his gf. Do you think it would be inappropriate to make my feelings/intentions known, now that he's back with his ex? For example, next time he texts me, mention that I have feelings for him, and may need some space? I truly am kicking myself for not sucking it up and making this clear before, and like you said, I don't think his current relationship is likely to last forever. If things don't last too long, I'd really like to have another chance at this and I think if I simply let him know my feelings before allowing distance between us, it can leave that door open. But I also don't want to cross any lines if it's inappropriate to say so when he has a gf, which is what I'm currently not sure about.

In the meantime, I will definitely take your advice to make myself available if another dating opportunity arises. I genuinely have feelings for him and can truly see a future together, but I don't want these "maybes" to prevent me from being able to meet someone else if he's no longer available.

Thank you :)

Your problem is that you didn't just ask the guy out. You go out on dates to find out if you have feelings for someone and if they have feelings for you. You don't tell them you have feelings for them and then ask them out. You've got it backwards. Try to keep that in mind in the future. And no, you don't tell him while he's dating someone else that you have feelings for him. That's just rude and bad form and very unfair.

Also, keep in mind, there's no harm in asking someone out. You get to experience the chance at rejection us guys go through. There's some websites out there that says girls aren't suppose to ask guys out, but that's nonsense. If you don't ask, you don't get. But you can also help a shy guy to know he has a chance with you by asking him out. Or you can play semi-shy and ask a guy to ask you out, such as, "So when are you going to ask me out?" Or, "So when are we going out for coffee?" Some guys need a push, especially Millennials who don't seem to know the tried and true dating rituals. But see what happens with him, but continue to live your life and keep busy until you find another guy or this guy becomes available.

How did he get you number? Unfortunately your friend was egging you on and being a busybody/matchmaker telling you "he's almost in love with you".

You did the right thing letting this go and not making a move. He was only being polite/friendly.

Why not get on some dating apps and try to ignore this friend's meddling or trying to make a fool out of you.

-He is 26 and I am 30.

-2 months we've been texting here and there

-he JUST got back together with his ex-gf,

Your problem is that you didn't just ask the guy out. You go out on dates to find out if you have feelings for someone and if they have feelings for you. You don't tell them you have feelings for them and then ask them out. You've got it backwards. Try to keep that in mind in the future. And no, you don't tell him while he's dating someone else that you have feelings for him. That's just rude and bad form and very unfair.

 

Also, keep in mind, there's no harm in asking someone out. You get to experience the chance at rejection us guys go through. There's some websites out there that says girls aren't suppose to ask guys out, but that's nonsense. If you don't ask, you don't get. But you can also help a shy guy to know he has a chance with you by asking him out. Or you can play semi-shy and ask a guy to ask you out, such as, "So when are you going to ask me out?" Or, "So when are we going out for coffee?" Some guys need a push, especially Millennials who don't seem to know the tried and true dating rituals. But see what happens with him, but continue to live your life and keep busy until you find another guy or this guy becomes available.

Thank you for the advice :)

You're right, it would not be appropriate to say anything now. After having a day to let the initial shock and sting wear off, I know I have to let things be. Should we both be single together, I will be able to learn from this. (I will say, I agree that you need to date to discover if there's feelings, but he and I worked together for a year, so there was definitely time for feelings to develop. But yeah, we'd have to date to see how deep they go).

I really hope I can build up the nerve to ask someone out next time I'm in this situation. You men are brave, I'll give you that!

How did he get you number? Unfortunately your friend was egging you on and being a busybody/matchmaker telling you "he's almost in love with you".

 

You did the right thing letting this go and not making a move. He was only being polite/friendly.

 

Why not get on some dating apps and try to ignore this friend's meddling or trying to make a fool out of you.

I don't think my colleague was egging me on (and absolutely not trying to make a fool of me). I'm sure there's some "busy bodies" out there who are like this, but this woman is very sweet and never been one for dramatics or to ever be hurtful. He just naturally came up in our conversation as we were catching up (the three of us worked in close proximity for a year along with a fourth person) and she eventually mentioned how much he likes me (he literally told her this, and that he regretted not making a move when he had the chance). I was shocked and said something along the lines of how I "had no clue" to which she responded about how he's practically in love with me because he's always bringing me up and saying that he missed me and wished he at least asked for my number before I left.

I gave her my number to pass along to him if he still wanted it. He texted me, which led to the back and forth texting I mentioned in my original post. I feel like maybe he was waiting for me to either initiate or at least bring up the feelings thing, which I didn't. I kept it pretty light and platonic (being so shy I couldn't bring myself to make the first move). So I worry maybe he got the wrong impression and that I only wanted to be friends. Or maybe he realized his feelings are not what they once were, and things naturally died off. Can't really know now, and that's on me for not being more straight forward. It's not the end of the world, but I do wish I could get another shot, as I think we would be really great together. Live and learn.

It's good you didn't get involved, given this situation.

I found out he got back together with his ex-gf