I’m a woman in my 20s, and I just moved to a new city to start grad school, and since I don’t know anyone here, I’ve been going to a lot of getting to know you events for people in my program. Because of COVID, most of these are outdoors and, with the heat, people dress pretty informally.
The other night, I was at a beer garden event and started talking to a nice, friendly, good-looking guy. As we kept talking, I looked at his T-shirt and noticed that it displayed one of those ironic, trying to be funny slogans that’s also actually offensive (in this case, specifically sexist). At the end of our conversation, he asked for my number, which I gave him. Should I hang out with him? And, if so, should I say something about the shirt?
Your question sure does hammer home the importance of first impressions! This guy showed profoundly bad judgment by wearing this shirt to a professional function. It’s also easy to speculate that he has poor judgment generally by owning and wearing an offensive shirt in any context. It’s also, hopefully, almost as easy to see how starting grad school and moving to a new place is an opportunity for reassessment and reinvention, and you may have a positive role to play for this guy.
You should absolutely say something. Maybe, “I enjoyed talking with you the other night. I also found your shirt to be offensive because of how it portrayed your attitude toward women. Before we decide to hang out, I wanted to let you know that and see if you would be open to talking about it.” Or, “I’d be glad to get coffee, but first I just have to ask — do you really think that shirt you were wearing the other night was funny?” Or, “Sure, but please leave the sexist slogans at home.” Assuming any such conversation will be happening over text, he’ll have time to think about his response, and you’ll learn a lot from what he says.
If you, understandably, decide you couldn’t bear to be seen one-on-one in public with someone who even owns such a shirt, I’d still urge you to consider being a positive influence in his life. Maybe there’s an adviser or other authority figure you could mention this to, letting them know you think he’s a good guy but worry that his lack of professional dress could be a problem moving forward. Or maybe he’ll make other friends who you can tip off indirectly about his shirt. Hopefully, this is the only one he owns, he wore it on a dare and you and he will both make lots of great, smart, thoughtful and professionally-minded friends during your grad school careers.
You could also do a serious slow-play here and not say anything at all, for a while. Depending on the size of your program, you may or may not see a lot of him. If you feel invested at all in this potential friendship, take some time to see what he says in class, how he behaves around you and your other classmates and, yes, what else he wears.
After you get to know each other, in whatever context that may happen, you’ll likely have a better idea of what you actually want to say and whether or not he’ll be receptive to hearing it.