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

There’s a aphorism that was coined by Robert Heinlein: Hanlon’s Razor. According to Hanlon’s Razor, you should never attribute to malice that which is adequately explained by stupidity. I don’t think your work flirt buddy is trying to string you along or is deliberately playing with your emotions. I think what’s far more likely is that he has no idea that you’re as invested in this as you actually are.

Something that a lot of people often don’t realize is that some people are just flirty. Just as some people enjoy making bad puns and others relate everything to sports, some people default to flirty behavior. It’s just an aspect of their personality, something they do because hey, it’s fun to flirt. The problem is that not everybody flirts for sport. Some people don’t appreciate being flirted with and some don’t appreciate people who flirt without intent. This misalignment can result in irritation and hurt feelings, especially if the flirter doesn’t recognize when someone else is taking it seriously.

(Although, pecks on the cheek and neck are just… well, hope he has better social calibration than he seems, because otherwise that’s a “yikes” from me, bro.)

Now that having been said, it’s also possible that there’s misalignment in other areas cropping up. The first is that you handed him your number and then told him that you’re not really a phone person. While I can’t speak for your coworker, to me, that would seem like some mixed signals. From the way you phrased it here, I think he might be forgiven for hearing “here’s my number, never use it.”

It’s also possible that he’s not comfortable talking on the phone. While it’s more common in millenials and younger generations, a lot of folks hate talking on the phone with the heat of a thousand suns. For them, texting is the way they prefer to communicate; someone calling on the phone feels awkward and makes them anxious. So you might have had better luck sending him a flirty text.

You might also have taken the initiative earlier than you did and made the first move yourself instead of waiting by the phone for him to call. While you may have had the same results – an uncomfortable and awkward conversation that went nowhere – at least you would’ve realized that this isn’t what you want or need.

Regardless, this series of near-misses, miscommunications or just plain incompatibility has lead to a point where you’re actively confused and upset. That’s why the thing you should do is what you should’ve done a while ago: use your words with this guy. While I understand your worry about appearing desperate, I think you’re well within your rights to say “Dude, what the fuck?” Trying to get some clarity isn’t desperate, it’s the first step in establishing some much-needed boundaries. If he’s a flirts-for-fun guy and you’re not a flirts-for-fun kind of lady, then the best thing you can do is say “I appreciate the flirting but if you don’t mean it, I don’t want it.” If he does mean it and he’s having his own debate of “wait, is she interested or not”, then now he’ll know where you stand. Then the two of you can try to hash out whether you want to give things another shot while everybody’s on the same page.

Pulling him aside and having a much-needed convo about just what’s going on, how it’s making you feel and how you would prefer to interact from now on will do you a world of good. It may not get you any meaningful answers, but at least you’ll have cleared up any lingering confusion.

Good luck.

Hi Doc,

I’ve been in the scene for a little over a year now after taking an entire quarter+ of my life off of dating. I’m 26 and coming around to the idea that I’m not a bad looking guy and that I have a certain charm. Anyway, there’s a girl. She’s a little younger and a lot more experienced. The problem: I live in Kentucky and she only lives here part time. After an amazing few dates, she left town for her other part time home on the west coast. She’s been there a week and a half now and won’t be back for three more weeks, and then she’ll be here for about four weeks, then off to the beaches again.
I told her I liked her and she said she liked me too. It’s casual because she does not live here and doesn’t know if she’ll even live in the US in six months. I knew that going in. But what I can’t take is the lack of communication. She doesn’t ever text me first and when I text her she replies like six hours later at best and it’s usually only a few words. I don’t even know if I should be texting her at all and that drives me nuts too. She said she would let me know when she’s back in town and ready to hang out, and that makes me wonder if I should even ask her out when she’s back. If she doesn’t ask me out I know I will have to – I’m not going to ghost myself – but I guess my question is, how can I make sure she’s still interested without putting her off? Last time I said I thought she was awesome over text she gave me a “haha” and the memory haunts me.
Relatedly, is it healthy to convince yourself that nothing is wrong and you’re just being anxious? I haven’t been able to do that but I’ve been trying. I’ve failed because I think too logically and I know that I cant be sure that nothing is wrong even if I know that at one point she liked me.
Dumb Idiot?

Alright, there’re a few problems here DI, and the first is that you’re seriously overinvested. Now I get it: you haven’t had much dating experience and you’ve hit it off with this awesome woman who thinks you’re a fair bit of alright too. It’s totally understandable that you’re a little twitterpated and all caught up in the thrill and novelty of it all. But the truth is that you’re giving this relationship far more importance and significance than it really deserves. You know, intellectually, that this is a relationship with an uncertain future at best and that you’re going to see each other sporadically, if at all.
Those are all signs that this isn’t the relationship to be putting as many emotional investments in. But that’s what you’re doing, which is exactly why you’re in the emotional state you’re in.
Right now, you’re putting far too much thought into the meaning of everything, especially for what is ultimately a fairly casual relationship, particularly a long-distance casual relationship. I strongly suspect that as much as you see this as casual, this is more casual for her than it is for you. You’ve invested more than she has and you’re expecting more in return than I think she has to offer. And I think you may know this at some level; that’s part of why you’re so caught up with reading the tea-leaves and trying to divine meaning from silence and the length of her replies. The conflict between what you’re hoping for and what you’re feeling is triggering your anxiety.
Part of why we all get so hung up on the “OH GOD WHAT DOES THIS ALL MEAN” is because of the ambiguity of the situation. You want one result but you feel like the other is happening and the tension between the two – that sense of uncertainty – is incredibly uncomfortable. You don’t want to be right, but you’re afraid you are and you’re trying to find proof you’re wrong. That’s why little things like an innocuous response to your text is keeping you up at night: you’re trying to make this fit between your hopes and fears.

Unfortunately, the answer to this is to collapse this particular dating quantum waveform and accept that she’s not into you the way that you’re into her. Yeah, I realize this is the opposite of what you’re hoping for. But here’s the thing: this will actually ease your anxiety. Having an answer, period, will settle you down. Yes, even when it’s not the answer you’re hoping for. The certainty will feel far better to you than constantly being on edge, trying to figure out where this is going and what you’re doing wrong.

Now this doesn’t mean that she doesn’t like you or won’t want to see you when she’s in town. It just means that she’s not looking for something that’s going to continue beyond when the two of you are in physical proximity to one another. If she’s in town, she’ll want to see you, but texting and staying in regular touch doesn’t seem to be what she’s looking for. If you want this to have a chance of working, then you need to adjust your expectations accordingly.
I think it may help to think of this as akin to a summer romance: glorious and exciting but temporary… but all the sweeter for its brevity. Don’t take it as a sign that you’re undesirable or unwanted, but as proof that there are people who dig you and what you have to offer. Take the thrill, the experience and the confidence you gain from this short term relationship and let that help power and motivate you as you look for something closer what you want in the long term… and possibly closer to home.
Good luck.

This post was previously published on and is republished here with permission from the author.

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