Adapted from a recent online discussion.
Aunt's jokes about not dating deserve a blunt response
Single: I'm 30, a woman, single and okay with it. However, I have to visit family soon and I'm not sure I will be able to be civil if my aunt once again jokingly suggests that I wear a sign on the subway that says, "I'm single and desperate!" (Not joking — she actually suggested that.) I am so tempted to say something rude and/or embarrassing to her, like, "Don't worry — I may be single, but I'm having plenty of one-night stands." Do you have any suggestions for a retort that would make me look great and her look crazy?
Carolyn: How about just asking, with complete seriousness, "Do I make you uncomfortable?"
Anonymous: What worked for me was to ask my mother, the sibling of the aunt, to speak with Auntie in advance and ask her not to bring it up. It worked so well that once I did meet my wonderful husband, I was not asked, "When are you getting married?" and throughout six years and counting of infertility have not been asked, "When are you having children?"
Carolyn: This does work — if the one being asked is reasonable and has a reasonable relationship with the messenger.
Your anecdote is a great reminder, though, that a lot of people are just trying to be friendly and don't realize they're crossing a line. It may seem as if your body language or facial expression would send that message for you, but some of us are better actors than we think, and some audiences are more clueless than we (or they) would like.
The ones who think they know better, well, no amount of intervention will deter them. Such entreaties work on them the way red capes do with a bull.
Weigh long-term vs. short-term risks in asking friend to date
Worth a shot? I (female, 28) have been friends with a male, 31, for three years. I recently started developing feelings for him based on learning more about our mutual life goals. I had never really thought of him as a potential mate but have learned more about him that makes me think we could be really happy together. Do I risk mentioning dating? Possible downfalls: (1) He could be totally not interested, thus embarrassing me; (2) He could be interested but we eventually break up and cannot be friends anymore. Or we could just stay friends but never know what could have been.
Carolyn: The potential consequence of doing nothing is missing out on something great. Long-term loss.
The potential consequences of speaking up are humiliation and a damaged friendship. Awkwardness and humiliation, pfft, those are along for the ride on anything, like a shadow, and they're likely short-term. Not legitimate deterrents.
Damaged friendship is a consequence to weigh carefully. Let's say you went out and then broke up in a way that precluded friendship. That would suggest imbalances/incompatibilities between you that would challenge the friendship anyway. Give it a little more time if you want, to give you a chance to read his interest in you, but try having in mind not whether you'll jump, but when.