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You might say they’re previous for a reason. Well, it’s me that did the dumping because I wanted to be free and enjoy the single life. And I was compatible with some of them. Looking back, I can’t believe I dumped them. I guess a relationship wasn’t so important back then.
Prior to meeting Mike, I had several men interested in me. They were also better looking than he is. But I was unfocused/selfish/immature, and I used to treat handsome guys who were interested in me with contempt. I thought I’d bump into them again like I always would at the local bar. I thought they’d still be single. But these men are now in relationships, so I missed my chance. How naive to think they wouldn’t meet someone else!
Mike is smart, has a good personality, and is very open. He ticks most of the boxes except he’s not handsome enough. He’s not ugly, just average looking. I sound crazy shallow, but I don’t believe I am. I’m just human. I suppose I want people to say “Hey, he’s handsome,” but they may not think that with Mike. He hasn’t met my friends or family as yet. If we continue dating, it will eventually have to happen.
I realize that looks fade and I’ll eventually age and so will my partner, but I thought I’d end up with a better-looking man. Do you think I’m settling? Do you think I can get past this?
FYI, we’ve booked to go on a short holiday together (a week). — A Bigger Catch
Do I think you, a 44-year-old single woman who has admittedly missed her chance at relationships with multiple guys because she was unfocused, selfish, immature, and treated men with contempt, is settling for a man who is smart, has a good personality, and is actually interested in pursuing a relationship with you? Hell, no! I think you’re lucky to have him, from the sounds of it. Honestly, HE might be settling to be with you.
You think 44-year-old single women who are entitled and shallow are in high demand? Because, I assure you, men are not usually clamoring for 44-year-old women who think they’re all that and deserve the most handsome and hottest. At 44, if you want the hottest guy in the room, you better be fucking stunning yourself. Like, movie star good looks. And if you have that, you still need to have the personality to go with it to attract a guy who is also the full package.
I’m not faulting you for not being attracted to someone (if that’s even the case), but I am judging you for prioritizing your friends’ and family’s opinions about the appearance of your boyfriend. I think it says a lot about your character and priorities that you place so much importance on your friends thinking your boyfriend is hot. That’s how teenagers think, not grown-ass women who are serious about wanting a committed relationship.
So… maybe you don’t want a committed relationship? Is that a possibility? You left other boyfriends in the past because you wanted to “be free and live the single life.” Is it possible that’s what you still want? Is it possible you keep looking for reasons to dump anyone who shows interest in you — even acting with “contempt,” as you say — because deep down what you really want is to be single and free? It’s worth thinking about.
Not everyone is meant to be paired up. Certainly, not everyone is meant to be paired up for the sake of being in a relationship. THAT is when you’re settling — when you commit to someone simply because it’s what you think you should be doing because it’s what everyone else is doing and it’s what society says is the normal thing to do.
What if… what if you remained single indefinitely? What if you kept dating around, but you gave yourself permission to not commit to any one person, to not call anyone your “boyfriend” and have all the strings that are attached to that title? You could still have the fun and companionship and affection without the pressure of being 100% compatible forever and ever. I wonder if that might free you up to enjoy and appreciate what a man can offer you without ticking boxes and comparing him to all the past boyfriends you left behind.
Rather than tell yourself you gave up pretty to settle for average, you could reframe it: You gave up the pressure of a committed relationship for the freedom of living single indefinitely. If that still doesn’t feel right to you though, I would strongly urge you to get some perspective and re-prioritize what you’re looking for. Looks fade. Good personalities, shared values, and chemistry last a lot longer.
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If you have a relationship/dating question I can help answer, you can send me your letters at wendy(AT)dearwendy.com.