So, I am recently divorced. It has been a few months, but, realistically, we have been done for a year, but now the ink is dry on the divorce papers. I am in my 40s, in good shape and not unattractive. I don’t know a lot of single people, don’t get out that much and I haven’t had a date in almost 20 years. Needless to say, I am a bit panic-stricken. I have decided, after a lot of harassment from my sister and my friends, to try Internet dating. It is overwhelming. Terrible. But I’m trying. So, here’s the thing: What is with women all looking for tall guys? Even the tiny ones—there are women who list their own height as five-two—insist on a guy being at least six-two! Why is this so prevalent? And what should I do? I’m five-eleven, and I’m not really prone to bullshitting anybody. Should I not bother to contact a woman if she’s asking for a guy who is six-two? Or should I contact her and tell her up front that I’m shorter? Maybe wait until we meet and let her figure it out herself? I know this sounds stupid, but I am totally new to this thing, and I don’t want to be a dick.

Too Short?

I think what you need to keep in mind here is exactly what kind of woman is that specific about who she wants to meet. Six-two? Really?! You are resorting to digital dating and you’re going to rule out any guy who is not up to this arbitrary standard? I can understand a particularly tall woman wanting to be with a guy who is taller than her. One of my best friends is five-eleven, and she said she already feels like a freak all the time and she needs to date somebody taller than her so she doesn’t feel even worse about herself. Even though I don’t agree with her, I’ve never had to walk a mile in her flats (because she’s too tall for heels, get it?) and I know her well enough to know that this is about her, not about her potential dates. But anybody who is five-foot-one and insists on your being six-two is probably a shallow dimwit who is not worth dating anyway. Consider that they have done you a favor and narrowed the field.

I am in a very frustrating situation. There is a woman that I work with whom I really like. We have been working very closely with each other on a project for the last year. We spend a lot of time socializing as well. We have talked about the fact that we are attracted to one another, but there is just no way that we can let this thing happen while we work together. It sucks. I am not exactly her boss, but her superior in a way that would make it really, really bad for my career if we started seeing each other and anybody found out. Also I am afraid she would be devalued and her work might be taken less seriously if people thought that she was being rewarded because of our personal relationship.

I have mostly put it aside. I am very busy anyway, and I have basically decided to just sort of ignore my feelings for her because there is nothing I can do about them. I don’t socialize with her outside of work or work-related activities at all anymore. The whole thing is weird, and for awhile it was painful, but I am getting over it. Now I have a new problem. I met another woman whom I am interested in. She is a friend of a friend, nothing to do with my job, not connected to anybody I work with at all. Perfect. And she is single, and she is interested in having a drink, which is great. But now I am not sure how to broach the subject with my co-worker. I feel like I am betraying her or cheating on her in some way, even though I know we can’t have a relationship. I don’t want to hurt her, but I don’t want to lie to her either, because I have too much respect for her. What is the best way to tell her?

Stand-Up Guy

Don’t get ahead of yourself here, SUG. I don’t think you need to tell her anything right away. It’s very nice of you to want to be straightforward, but do you really want to make a potentially painful announcement when this thing might not last more than one drink? I’m not trying to be negative, just practical. If you tell her about the date and nothing happens, and then you tell her about the next person you ask on a date, and then the next, it may come off like you’re trying to rub it in, or worse, make her jealous. Give it a minute. Go for the drink. If it goes well, meet up for another drink, or go to dinner. If you feel like this is a person you are going to actually start seeing, then you sit your co-worker down sometime when you aren’t at work, and tell her what’s going on. Start with “I’ve met somebody.” Explain to her that you feel awkward telling her, but that you don’t want to hide it from her, etc. Tell her you wish things could have been different between you but that you don’t see any way around it. Then hope that she also meets somebody else and you can both move on and be happy and not have any regrets.

Confidential to Player, Hater: That book is stupid. The rules are stupid. And yes, sadly, they do often work. If you insist on reading that tripe, try not to use it as a manual for how to treat women as much as a kind of structure to use to keep social situations from becoming awkward for you.