Co-Worker - When you think he likes you back, but just can't be sure! Update p8

[Spoder]

Okay, I'm not the OP (obviously  ) but I'm jumping in here on her behalf, sort of.

People always say that if a guy is interested, he will grab the chance to spend time with you. So, the OP put out feelers re: the concert and the coffee thing, and he didn't bite. Okay, I get that maybe the Starbucks invitation didn't count, but the concert - really? He mentioned that he wanted to go to this concert on Saturday night and asked about her weekend plans, she said she was only free on Friday, and he never asked her to the concert?  That would totally be my point of assuming that he's just not that into me.

So people think she still kind of messed up by not explicitly asking him out? I would have thought that she was ignoring all cues if she *did* ask him out.

FWIW, I'm not trying to be argumentative, at all - I'm genuinely curious.

[Samgirl2]

Okay, I'm not the OP (obviously  ) but I'm jumping in here on her behalf, sort of.

People always say that if a guy is interested, he will grab the chance to spend time with you. So, the OP put out feelers re: the concert and the coffee thing, and he didn't bite. Okay, I get that maybe the Starbucks invitation didn't count, but the concert - really? He mentioned that he wanted to go to this concert on Saturday night and asked about her weekend plans, she said she was only free on Friday, and he never asked her to the concert?  That would totally be my point of assuming that he's just not that into me.

So people think she still kind of messed up by not explicitly asking him out? I would have thought that she was ignoring all cues if she *did* ask him out.

FWIW, I'm not trying to be argumentative, at all - I'm genuinely curious.

Thanks! Just to clear up, I think you mean I told him was only busy/had plans on Friday night.

Yep, he told me about a concert, said it was saturday, asked if I had weekend plans, I said ''only on friday night" and he switched the conversation to what those plans were on the Friday night and never mentioned the concert again.

I told him it sounded fun, I'd said I was free. He could have said, well if you're free saturday how about coming with me. But he didn't and I've always been of the opinion that if a guy is interested he will make the first move. So hopefully people can see why I would see that as he's not interested?

[Spoder]

Okay, I'm not the OP (obviously  ) but I'm jumping in here on her behalf, sort of.

People always say that if a guy is interested, he will grab the chance to spend time with you. So, the OP put out feelers re: the concert and the coffee thing, and he didn't bite. Okay, I get that maybe the Starbucks invitation didn't count, but the concert - really? He mentioned that he wanted to go to this concert on Saturday night and asked about her weekend plans, she said she was only free on Friday, and he never asked her to the concert?  That would totally be my point of assuming that he's just not that into me.

So people think she still kind of messed up by not explicitly asking him out? I would have thought that she was ignoring all cues if she *did* ask him out.

FWIW, I'm not trying to be argumentative, at all - I'm genuinely curious.

Thanks! Just to clear up, I think you mean I told him was only busy/had plans on Friday night.
Yep, he told me about a concert, said it was saturday, asked if I had weekend plans, I said ''only on friday night" and he switched the conversation to what those plans were on the Friday night and never mentioned the concert again.

I told him it sounded fun, I'd said I was free. He could have said, well if you're free saturday how about coming with me. But he didn't and I've always been of the opinion that if a guy is interested he will make the first move. So hopefully people can see why I would see that as he's not interested?

Oh yeah, sorry, I did mean that!

So yes, I can't see what else you could have done. (Don't take my word for it, though - I'm probably totally wrong, which is why I'm hoping someone will come back and clarify!)

[EduardosGirl]

OP, I think it boils down to this: if you're not willing to ask him out - clearly and without confusion - you need to let this go and move on.

I know it's not easy to put yourself on the line like that. It's hard! The risk of rejection can feel crippling. BUT! Even if he says no, whoever he is, that doesn't diminish your own amazingness. It just adds nuance to it. And it gets easier. The first time you do something is always the hardest.

So, if you can only accept him asking you out as an opener, I think you need to cut your losses and assume the role of his supervisor.

[Samantha]

I can see where if he asked if you had plans this weekend, and you only mentioned Friday ("Oh, I am doing XYZ on Friday night"), and YOU never specifically mentioned Saturday, ("...but I have nothing planned for Saturday or Sunday yet.") he might not suggest something for Saturday, because he could have thought that by you not specifically mentioning that day, you were implying that you already have plans that you don't want to talk about for whatever reason. Sure, he should have taken that ball and ran with it ("Well, what about Saturday? Would you like to attend the concert that evening?"), but he didn't. He could be viewing it as he brought it up, and YOU didn't reply in a positive manner about the concert, and so he didn't say anything further about it.

One of you needs to make a very clear move, one way or the other. Skirting the issue and hinting is clearly not working, so make a move on him, or move on.

[gramma dishes]

People always say that if a guy is interested, he will grab the chance to spend time with you. So, the OP put out feelers re: the concert and the coffee thing, and he didn't bite. Okay, I get that maybe the Starbucks invitation didn't count, but the concert - really? He mentioned that he wanted to go to this concert on Saturday night and asked about her weekend plans, she said she was only free on Friday, and he never asked her to the concert?  That would totally be my point of assuming that he's just not that into me.

So people think she still kind of messed up by not explicitly asking him out? I would have thought that she was ignoring all cues if she *did* ask him out.

You know, I kind of agree with this.  I think she HAS put all kinds of feelers out there and he just isn't picking up on them.  Either intentionally because he just isn't that interested in dating her, or unintentionally because he's just so afraid of possible rejection and the subsequent embarrassment and humiliation that he isn't willing to make the effort. 

If he isn't interested "that way" in her, then she would only put both of them in an uncomfortable position by making the first move.  If he actually is that interested, would you really want a boyfriend who is so incredibly chicken and insecure that he's afraid to even ask you for one date?

I trust the OP has a sensitivity to which situation applies here (if either) and will make the decision that's best for her.  Congratulations, OP, on your new job!

[TurtleDove]

If he isn't interested "that way" in her, then she would only put both of them in an uncomfortable position by making the first move.  If he actually is that interested, would you really want a boyfriend who is so incredibly chicken and insecure that he's afraid to even ask you for one date?

For some of us, it doesn't make sense that the man would be the only one with responsiblity here.  If I am interested in someone, I ask them out (if they haven't asked me already).  I don't think I have ever been turned down. (I am a woman).  But if I were, I don't think it would crush me.  I have turned down countless men, and I have done it so they still felt good about themselves.  I cannot imagine this guy would do anything to hurt the OP, even if he is not interested romantically.

[Judah]

If he isn't interested "that way" in her, then she would only put both of them in an uncomfortable position by making the first move.  If he actually is that interested, would you really want a boyfriend who is so incredibly chicken and insecure that he's afraid to even ask you for one date?

For some of us, it doesn't make sense that the man would be the only one with responsiblity here. If I am interested in someone, I ask them out (if they haven't asked me already).  I don't think I have ever been turned down. (I am a woman).  But if I were, I don't think it would crush me.  I have turned down countless men, and I have done it so they still felt good about themselves.  I cannot imagine this guy would do anything to hurt the OP, even if he is not interested romantically.

This is what it is for me.  Maybe he's not interested, or maybe he is and feels that he hasn't gotten a clear signal to take the next step.  But why is it his responsibility to take the next step?  It's hard to ask someone out and too many women lay all the responsibility of doing it on the man, but she is perfectly capable of asking him out and won't.

OP, it doesn't matter to me one way or other, but if you want to go out with this guy ask him out.  If you don't want to go out with him, don't ask him out and stay in the friend zone.

[LifeOnPluto]

I think (from talking to male friends, etc) that guys are happy to be the ones doing the asking. But only if they're at least 90% sure the girl will say yes.

It sounds like Samgirl might not have been clear enough in sending the message that if he were to ask her out, she'd say "yes".

I also think there is a level of interest from this guy - eg buying her her favourite lollies as a surprise, etc. To me, that's not something a person who is "just a friend" would do. I actually think it would be a little disingenuous of this guy (at this point) to suddenly turn around that claim that he saw the OP as nothing more than a friend, and that his actions were perfectly friendly, nothing more. 

[Starchasm]

Okay, I'm not the OP (obviously  ) but I'm jumping in here on her behalf, sort of.

People always say that if a guy is interested, he will grab the chance to spend time with you. So, the OP put out feelers re: the concert and the coffee thing, and he didn't bite. Okay, I get that maybe the Starbucks invitation didn't count, but the concert - really? He mentioned that he wanted to go to this concert on Saturday night and asked about her weekend plans, she said she was only free on Friday, and he never asked her to the concert?  That would totally be my point of assuming that he's just not that into me.

So people think she still kind of messed up by not explicitly asking him out? I would have thought that she was ignoring all cues if she *did* ask him out.

FWIW, I'm not trying to be argumentative, at all - I'm genuinely curious.

Yeah, honestly I think he's not that into you and if you DID ask him out you'd be ignoring the signals.  The fact that you're his superior makes it an even better idea to not ask him out directly.  If he's not picking up what you're putting out then it's not meant to be.

[bah12]

These updates are frustrating to read, because what I'm understanding is two people fishing for some "extra" time together, but waiting on the other one to both take the bait and reel the deal in.

I think instead of him saying "I'd like to take advantage of the good weather for lunch and go somewhere," he should instead say, "Hey, how about we take advantage of the good weather and go out to lunch with me?"

Instead of saying "I want to go to a concert on Saturday but don't have tickets yet" he should say "There's a concert Saturday night that I want to go to...if you don't have plans, would like to go with me?"

But, since he's not the one asking for advice, I'll tell you this.  Be more clear.  When he mentions lunch...don't suggest a coffee shop to look over work stuff.  That's not asking him out to lunch, that's suggesting that instead of walking outside to review documents, you go to a coffee shop to do it instead.

When he mentions a concert that he wants to go to and asks if you have plans for the weekend say "I have nothing planned for Saturday and now that you mention it, that concert sounds really great.  Do you want to go together?"

It's possible that he got stuck asking you about Friday night because he wanted to guage if your plans included a date with someone else. It's also possible that because you like him, you're reading into everything that he says and does as possible clues that he likes you back but because they aren't real clues, you read them as "mixed signals" instead of what they really are.

But, the truth is, you aren't giving him any ammunition to ask you out with.  I used to be this way too.  I'd like a guy but was too scared to show it, so instead of just admitting it to him or giving him clear signals, I would act like I was fine with the relationship the way it was and I would be the one sending mixed signals.  It's a self-protection thing...I get it.

I think that you need to decide two things and then move forward.  One, do you like him enough to just come out and let him know that you want to go out?  And, if it turns out that he isn't interested, do you think you can work with him without any awkwardness?

If the answers to those questions are "yes", then ask him out.  Be clear.  Don't wait for him to figure it out and get the guts to do it.  "CW, there's this great new restaurant that I want to try.  Would you like to join me there for dinner one night after work?"

[Petticoats]

I would have suggested the OP making a move with a better late than never view (doesn't sound like co-worker has yet planned to move, and is considering the possibility), *but*, OP mentioned that with a recent promotion she now has authority over his schedule (possibly other work matters also).  What may be done in pursuing personal relationship possibilities (asking someone for a date) between peers is not always as possible or advisable objectively, or ethically where it involves colleagues one of which has authority over the other.

I'd been rooting for the OP that this would develop from a friendly office relationship and would blossom into romance, but with her recent professional promotion, that changes the balance of what I would suggest she consider initiating.

Yes, I share this feeling. OP, is this guy someone you think would go to HR with a complaint if you asked him out (on a real date) and he didn't want to go?

[prairie_dances]

OP are you going to be directly his supervisor? If so, that might make things a little awkward. That said (I don't think you are officially his supervisor yet?), I agree with the other who said you should just ask him out or move on. From your updates I think there is a general interest from him for you but you both are avoiding directly asking each other out. If you really like this guy just say, would you be interested in going to a movie, dinner etc after work this week? He can say yes or no, either way you'll know.

I hope it works out

[cbcb]

These updates are frustrating to read, because what I'm understanding is two people fishing for some "extra" time together, but waiting on the other one to both take the bait and reel the deal in.

I think instead of him saying "I'd like to take advantage of the good weather for lunch and go somewhere," he should instead say, "Hey, how about we take advantage of the good weather and go out to lunch with me?"

Instead of saying "I want to go to a concert on Saturday but don't have tickets yet" he should say "There's a concert Saturday night that I want to go to...if you don't have plans, would like to go with me?"

But, since he's not the one asking for advice, I'll tell you this.  Be more clear.  When he mentions lunch...don't suggest a coffee shop to look over work stuff.  That's not asking him out to lunch, that's suggesting that instead of walking outside to review documents, you go to a coffee shop to do it instead.

When he mentions a concert that he wants to go to and asks if you have plans for the weekend say "I have nothing planned for Saturday and now that you mention it, that concert sounds really great.  Do you want to go together?"

It's possible that he got stuck asking you about Friday night because he wanted to guage if your plans included a date with someone else. It's also possible that because you like him, you're reading into everything that he says and does as possible clues that he likes you back but because they aren't real clues, you read them as "mixed signals" instead of what they really are.

But, the truth is, you aren't giving him any ammunition to ask you out with.  I used to be this way too.  I'd like a guy but was too scared to show it, so instead of just admitting it to him or giving him clear signals, I would act like I was fine with the relationship the way it was and I would be the one sending mixed signals.  It's a self-protection thing...I get it.

I think that you need to decide two things and then move forward.  One, do you like him enough to just come out and let him know that you want to go out?  And, if it turns out that he isn't interested, do you think you can work with him without any awkwardness?

If the answers to those questions are "yes", then ask him out.  Be clear.  Don't wait for him to figure it out and get the guts to do it.  "CW, there's this great new restaurant that I want to try.  Would you like to join me there for dinner one night after work?"

THIS!!!! this this this this this. Can't agree more!

Regarding the supervisor thing, regardless of who's asking it's awkward. But there are level of supervisor and with the tip-toeing it seems like you are doing, I wonder if you might end up both viewing is as more of a conflict than it is - another reason to not risk a direct "ask-out". Seriously think about whether it's a real concern, or an excuse.

[Samgirl2]

OP here.

First to answer a couple of questions posted above:

• I will be his supervisor in terms of discussing his schedule and coordinating stuff for activities he will be doing and working with him to make sure tasks get done. This is what I have pretty much been doing already anyway.  We both need to work together to get the tasks done.  However my boss (or soon to be official boss) is his actual boss. Basically it's because he's freelance and so comes in 2 days a week on a pretty high rate of pay and even though I am working with him and need to ensure stuff is done for my own workload, she wants me to keep an eye on him basically, to make sure he's busy and earning his money!  Any actual management decisions or issues would be her responsibility, not mine.
• No he's not the type who would go to HR about 'unwanted attention' if I asked him out.

I think it could be possible I like him and so am over analysing what he says/does, but at the same time he really seemed like he liked me that way.  Even my boss has asked me about it because she hoped something would happen (not often a boss says that!). Two other colleagues have told me, totally without me saying anything to them, that they've seen us around working together and asked if we were dating because that was the impression they got from the way we worked together and the way he looked at me so I feel like there is something there, but maybe he's just not into me as much as I am to him.

I totally get the advice about allowing him to see it's ok to ask me and me making the first move if I really want to know.  I think one of the reasons I really want him to make the move is because he is really laid back and easy going.  With that is the fact he lives in nearest city and has no car while I live in nearby small town. Now he's asked if there's a station where I live and how far to my house, but I want to know he can put some effort in.  I feel like if he can't even ask me out, will he be committed enough to carry on a relationship when he has to get on a 30 min train and a short bus ride to see me. Would he say yes if I asked, because it was easier, and if it started to go somewhere, would I be the one doing all the running IYKWIM?

I guess I really like him but I want to know he is serious, not just messing around.

This week he asked me about my plans for the days he wasn't in the office and I told him I had Thurs + Fri off to celebrate my birthday and see folks etc. He has my phone number and we've texted a bit. I guess I will see if he bothers to wish me happy birthday.  But.......yesterday he was eating his lunch at his desk and being very quiet looking at the computer. I asked what he was reading and he very casually said 'oh, just a few profiles'. I looked across and he was on a dating site! I didn't know what to say so I think I just casually said oh right, or something dumb.

But I think, if he can be actively internet dating and yet not asking out the single girl sat right next to him, who he has very definitely flirted with, then maybe he's just entertaining himself while at work and who knows what he's doing on his own time!