Hi Dr Nerdlove!

I’m an older-than-I-want-to-say woman. There’s a guy at my job who is the same age. We’ve been flirting for probably about a year now. I always took it as ‘play’ flirting, although he would occasionally mention that I hadn’t given him my number, his weekend could have been better (wink, wink), etc. I was reluctant because I wasn’t sure I was into him. Plus, I worried that we might end up hating each other if we tried to connect on a different level (hey, it happens sometimes).

About a month and a half ago, my feelings began to change. He has been really affectionate; always coming in for hugs and giving me sweet pecks on the face and neck. I thought he was really sweet and attentive. So I decided to give him my number. But, it was after I told him why I had been reluctant (didn’t want us to hate each other), and mentioning that I’m not really a phone person.

Well, he didn’t call me. I chalked it up to probably having scared him off, and didn’t take it personally. I privately teased him a little about being scared off, and things were basically the same. (For the record, to my knowledge, there’s maybe only one other person who knows about he and I). About two weeks later, he approached me and said he would call me. I was excited; I was off that weekend and hoped we could maybe spend a little time beginning to get to know each other better.

Well, he didn’t call me. I was a little pissed. I felt like he was trying to make a fool of me; just wanting to see how far I would take it. While I didn’t cease communication, I was distant. It was evident I wasn’t pleased. But he remained the same. He continued to reach out to me. Eventually I let it go and things went back to the way they’d always been.

In fact, things seemed to get even better. I should mention that I had never asked/confronted him about not calling me. I didn’t want things to be awkward at work for either of us, and I didn’t want it to seem like I was running behind him.

So the flirting seemed to intensify, and I finally felt comfortable enough to ask him why he never called. He said he’d lost my number. He then proceeded to give me his number. He seemed sincere and I was thrilled. Again, it was my weekend off and I had the same hopes as before.

That was Friday. I called him Saturday afternoon. I immediately sensed a shift. While I don’t think he was physically with someone based on some things he said, it was immediately evident that he wasn’t thrilled to hear from me. We talked about 15 minutes, he ended the conversation, and he didn’t indicate any interest in continuing phone contact. I was hurt and embarrassed. I decided that I was done. I don’t know if he has someone, just isn’t interested in me, or a little of both. Either way, it’s clear he’s not interested. It sucks, but that’s life.

The problem is he continues with the same degree of flirting. Initially I didn’t think I had an issue with this, but I find myself becoming increasingly depressed (this isn’t the only reason for this, but it’s in the top three). I have tried distancing myself from him, which isn’t too difficult at my job, but he seeks me out. He definitely notices that I am distant and goes out of his way to reach out. I believe my issue is that twice I have given him the benefit of the doubt, continued to play along, and both times been disappointed, rejected, and hurt. I’m reluctant to play along again. I feel like the joke is on me but I’m not in on it. He dangles a carrot in front of me and when I reach for it, he snatches it away.

I honestly don’t know what is up with him. I’m afraid to ask for fear of seeming desperate and of getting my feelings hurt. And frankly, it doesn’t matter. He’s obviously not into me. My question is: what do you think is going on with him, and how should I navigate this minefield at work? I don’t want things to be awkward and uncomfortable. But I also don’t want my heartstrings tugged and trampled every day.

Maybe Yes Maybe No

[Read more…]