For about two years, I worked in an office with this guy “Josh.” We ended up getting assigned to a few projects together, and whenever we were working together, we always got along fabulously. So I admit, I started developing pretty strong feelings for him. I never did anything about it, since we worked together, but when I decided to take a new job, I figured maybe something could happen. I never actually knew if he felt the same way about me, but any time we were together, we were always flirting.
About a week before my last day, a bunch of my coworkers and I went to happy hour. Josh was there, too. Pretty much the whole time that we were there, he and I had our own conversation going. I’m pretty sure everyone noticed the rapport we had, too. And I’m sure it didn’t help when Josh turned to another coworker near the end of the night and said, “Oh I god, I’m gonna miss [my name] so much. Seriously, I just love her. Isn’t she just the most amazing girl?”
Of course, I was totally excited to hear that, and throughout my last week of work, I was expecting him to ask me out. Well, he never did. And now, it’s been about three weeks since I left the job, and I haven’t heard a thing from him. I’ve texted and emailed him a few times just to say hi, and he always responds, and it’s always our usual flirty banter. But, that’s it. He’s never initiated the text or email himself.
So am I over-thinking things? Was he just being flattering to me? Did he really “love” me? I think about that night and what he said all the time, and I just don’t understand what he could have meant by his words. What should I do? I feel like maybe I should call or at least text him and ask him about what he said. But then I’m not sure if I’d be too forward and aggressive. If he really liked me, he would have asked me out, right? Maybe I just need closure, because I keep hoping that he actually has feelings for me, but maybe he doesn’t after all.
LemonVibe 
[Sounds like he was just being flirty to me.
[I came on here to say what everyone else has said: just ask him out already. If he says no, well, you don’t work with him anymore so you don’t have to see him anymore. No big deal.
[I’m with everyone else – what’s stopping you from asking him out? Maybe he’s wondering why he’s getting all these flirty emails from you, but you’re not making a move.
[Yes, you’re overthinking things. I’m guessing he’s not going to take your relationship to any other level than what it’s been unless he feels there is good reason. If you are still interacting with the same sort of banter, then in his mind things are the same as they were. How would he know you’re interested in a potential romance unless you’ve changed the game yourself?
[Grow some balls and ask him out.
Wait, I mean… don’t do that. He may not appreciate there being four balls between the two of you.
Channel some estrogen and ask him out. Or something like that.
[Seriously? You would let this guy you are obsessing over “go” without asking him out?? You don’t work with the guy anymore, what do you have to loose??
[I had to do a second read through of this, because I thought I accidentally skipped over the part where you were at the end of your rope because you had asked him out and he had brushed you off or something. But now that I realize I didn’t miss out on anything the first time, WHY CAN’T YOU ASK HIM OUT YOURSELF?
It sounds like he’s into you, but it is very possible that maybe he’s not. Maybe he has a girlfriend, or maybe he just likes someone to flirt with and you’re convenient. Or maybe he’s madly in love with you and is too afraid to make the first move. Maybe he’s sitting at home, over-analyzing all of your actions and wondering if he’s misinterpreting the signals.
Luckily, there is someone who can tell you all of this. I’d completely skip over the part where you ask him to explain what he meant by that comment, and I’d shoot him yet another flirty text or email. This time, however, give it a little more purpose. “Hey, I miss not seeing your handsome face at work every day. Want to do X, Y, or Z sometime and catch up?”
Your motives are clear, and ball is in his court. If he shrugs you off, or only keeps up the flirting without actually making any plans, maybe he’s not interested in pursuing anything with you for whatever reason. But at least you’ll have closure, and you’ll feel better about moving on without wondering about all the what ifs.
[You’re undergoing what I like to call “analysis paralysis”. I’ll echo everyone else by saying that you really should stop overthinking, and get to doing something about it. If you like this guy, what have you got to lose by asking him out? If he says no, will it be the end of the world? Sure, it may sting if he says no, but at least you’ll know for sure, and you can stop torturing yourself with “what-if”s. 🙂
[It’s possible he may only think of you as a fun cool girl to hang out with with no romantic intent. Is he flirty towards other female coworkers at all? Does he flirt with you only? But you’ll never know unless you try, as Margaret Charles said. What do you have to lose? If he doesn’t want to hang out, then you won’t have to see him again since you don’t work with him, right?
[I do this all the time, so I don’t blame you for wondering what’s going on and driving yourself crazy over it…but if there’s anything I’ve learned in the last, oh, three weeks, it’s that you’ll never know if you don’t actually ask him out! So, I agree with everyone else – just ask him to go do something and make it clear that you’d like to see him outside of work. Then see what happens.
Last thing I’ll throw out there, just to cover all the bases (no pun intended): are you sure he’s single? If you know that for a fact, then full steam ahead.
[Yes, you ARE over thinking it. It was the end of the night, he had had some drinks, and started with the “I love you man” schpeel.
Now, that being said, it sounds like you guys really do have something. So, in the interest of finding out what that is… ASK HIM OUT! Don’t text, don’t email, call him. Tell him you miss working with him, and would like to go out to dinner.
If he brushes you off after that, you have your answer. Until then, stop dweeling and discover the means to fix your problem!
[Well, sure if he really liked you, he’d ask you out. Or if he really liked you, he’d be absolutely terrified that you might reject him, so wait for you to basically give him 100% proof of your “yes.” Or he might just have been a little buzzed and affectionate towards a work friend. Or maybe you constantly save his ass at work, and that’s the context.
You can keep going like that for days on end (and apparently you have). 😉 The only way to know for sure how he feels is to do what the other commenters have suggested: woman up and tell him exactly what you’re thinking. Whether that’s actually asking him out or explicitly letting him know that you’re interested (the first option is actually a great way to do the 2nd), that’s up to you. But you can either play your cards or walk away, because what you’re doing now will eat at you for a very long time and really isn’t worth the mental anguish you’ll put yourself through.