Listen Up, Ladies: Here's Everything Real Men Think Is Wrong With You

[Jim Lane]

25. Question about a man commenting on a woman’s appearance

My question isn’t about broader issues of patriarchal control, but about my interaction with a specific woman. She and I had had a fairly casual acquaintance when I asked her out on a date. I came to her apartment to pick her up and she was wearing makeup, which she had never done the other times we met.

On the one hand, I definitely got a charge out of the idea that she was sufficiently attracted to me to make that extra effort. (Yes, just her accepting the date should have been enough. It wasn’t – but this post isn’t about my self-confidence problem.) Not only was I pleased by this, but, when someone’s made an effort, it seems courteous to give a compliment. The linked article notwithstanding, I think many women on many occasions like to be told that they look great tonight or that their new hairstyle really suits them or whatever.

On the other hand, I happen to prefer a natural look. I thought this woman had looked better all the other times I’d seen her, when she wasn’t making an effort.

So, I didn’t want to compliment her and make it more likely that she’d keep going this route, but starting off a first date by criticizing her makeup didn’t seem like a good idea either.

What should I have done?

I was going to conclude this post by recounting what I actually did. On reflection, though, I decided it might be more interesting to hear the thoughts of people who are writing on a clean slate.