Adapted from a recent online discussion.
My boyfriend and I have been together for two years; he’s a few months shy of 28 (I’m 30). It seems that the only clothes he wears are T-shirts, gym shorts, and Chucks, stuff I would consider vastly more appropriate for someone in their late teens or early 20s. If it was just around the house or for quick errands, I wouldn’t really care, but this extends to going out to dinner or for public events. (I put my foot down for an occasion at the Kennedy Center.)
Is it unfair to expect him to start putting a little more care into his dress at our age? I try not to nag, but it’s a little embarrassing to stand out so much from the other patrons of the reasonably nice restaurants we frequent in image-focused Washington, D.C.
It’s as much about self-respect — yours and his — as it is image-focus or the restaurants you frequent.
So it’s certainly fair to say your piece to him once, out loud, clearly; then listen to his answer; then use it to decide whether his clothes are the hill you want to die on.
“If it was just around the house or for quick errands, I wouldn’t really care, but your wearing T-shirts and gym shorts and Chucks when we go out to dinner or for public events is embarrassing to me, since we to stand out so much from the other patrons of the nice restaurants we frequent. Is it unfair of me to ask you to start putting a little more care into your dress, since we’re not teenagers anymore?”
Here’s why his answer will tell you more about him than an excessive fondness for gym shorts: To make choices that reject norms is bigger than just a T-shirt. He is certainly entitled to reject all the norms he wants, but you are also entitled to decide that someone who rejects norms that thoroughly isn’t the person you want at your side through life. You can decide that respect for the norms of your surroundings is a form of respect for the institutions and the people maintaining them — for the people working at the restaurants, for the people running and performing at the theater, etc. Different values are the single most valid reason to decide someone isn’t for you.
Plus, values aside, you’re free just to be sick of being out with the guy in gym shorts, and break up with him just for that.
Offer to buy him new clothes. My now-husband was like this too when we first started dating. Turns out he was terrified of shopping. I started buying clothes for him, he would wear them: win/win.
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