I have gone on more dates than usual in the past two weeks. In fact, I’ve gone on dates with three different men. 

I am physically attracted to one of them. He flirts with me, too. The other two are nice, but I don’t find myself physically attracted to them. Furthermore, neither of them really flirts with me. I think it is that they aren’t practiced in it and/or don’t know how moreso than they lack attraction to me. 

The one I am physically attracted to lacks a college education, he didn’t vote, and he doesn’t like to read. These things are… not great. 

I know that looks aren’t everything and that attraction can grow over time, but part of that attraction, at least for me, is flirting and banter. A personality and sense of humor can make a person very attractive. I’m just not feeling it. 

I am left with a dilemma. Do I continue to see these men and hope an attraction grows or do I cut them loose? 

Part of the issue is that it’s hard for me to see myself. I still think that I am much larger in my head. And because of that, I think that I only deserve who will have me, regardless of what they look like and whether I’m attracted to them. 

I realize this is a fucked up way of viewing myself. I’m not saying that I act on those thoughts in terms of sex or whatever; however, there is a part of me that is reluctant to let such guys go because who am I to say I deserve anyone better? I’m going to work on it in therapy, trust me. 

I have a feeling that, if I was to enter a relationship with one of these men, they would love me a lot. And I wouldn’t have to worry about them straying or looking elsewhere. But I don’t think I would be happy. I know that is a quick judgment based on two dates and a few weeks of conversation. 

Mitt and I continue to talk daily for hours at a time. We see each other every now and then, enjoying each other’s company in a friends with benefits way. 

Feeling uncertain of my attractiveness, I asked Mitt, “You think I’m attractive, right?” I then added, “The question is related to my inability to see myself.” 

I thought that he would say something like “You always look nice” or “The thought of having sex with you turns me on.” 

That was not the answer I received. 

Mitt chose to be brutally honest:

I like having sex with you, and there are things about you that I find sexy. I think you have a cute face (someone agreed with me on that when I forwarded your picture before seeing you for the first time). But, overall, I don’t find you that physically attractive. :-/ I feel bad saying that, but also don’t want to lie.

He didn’t want to lie and he couldn’t think of a gentler way to tell me this. 

After I expressed that I was quite hurt by his brutal honesty, I explained that what he said was basically like, “You have trouble seeing yourself? Why, you should see yourself as physically unattractive – just like I do!” I felt he was telling me that he finds me repulsive. I felt like I was just a cum dumpster. 

I realize that is not what he meant, but boy did it hurt. It wounded me. And it’s not like I was oblivious to the fact that I’m not his type. I am not an oblivious idiot. 

He tried to repair my hurt by listing my more positive qualities and the things that he did find sexy. He said he didn’t mean to hurt me, that he could have lied, and so on. 

I explained that I wasn’t looking for him to tell me he found me physically attractive. I was looking for him to tell me I was attractive, period. Generalities. 

We continued to unpack what was said. He basically told me the brutal truth because he did not want to lead me on. He didn’t want me to catch feelings or amp up feelings. We had agreed, after all, to a mutually beneficial arrangement and that this would not be a relationship. I was not under the delusion that there was any possibility of there being an us or of him being my boyfriend. Mitt doesn’t hold my hand or even walk at my pace when we’re walking somewhere (he has much longer legs than me). 

In the five months or so that I’ve known Mitt, I came to the realization that we would be miserable as a couple. I guess I failed to communicate to him — even in the midst of my sharing with him about my dates and us discussing at what point we’d have to lose the “with benefits” part of our friendship — how I considered us ultimately incompatible. He is hardcore outdoorsy and I prefer the outdoors in doses. I am hardcore about pop culture and media and he dislikes that stuff to the point that I think he looks down on me for it. I am a nester and I like stuff, whereas he is more of a minimalist to the point that he only owns two bath towels. He doesn’t even like stand-up comedy or rock music. I don’t particularly like long hair on men or general messiness. 

Granted, we are between a 96-99% match on OKCupid, so go figure. 

I wanted him to basically reassure me – as a friend (and someone who has seen me naked) – that I am an attractive person. After I clarified that I believe we have no long-term compatibility and that I do not want him to be my boyfriend, he was a lot more willing to say, “You are not repulsive, and there are people out there who will find you attractive, fun to be with, and can fall in love with you” as well as “You are lovable, and some guy will be lucky to have you.” 

We were able to work through what he said. Still, nothing makes you feel more like just a receptacle than being told that the man you’ve been sleeping with doesn’t find you physically attractive. 

FWIW, I was messaging with Same Dude Different Day at the same time. He answered my question without hesitation – yes, you are attractive (and he’s seen me naked, too! Ha!). That’s why I keep him around and why he’s one of my best friends. That and he checks in to make sure I haven’t been murdered when I’m on dates. 

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