Tell Me About It: A single niece and her crazy aunt

Question:

I'm 30, a woman, single, and OK with it. However, I have to visit family and I'm not sure I will be able to be civil if my aunt once again jokingly suggests that I wear a sign that says "I'm single and desperate!" (Not joking - she suggested that last summer.) I am so tempted to say something 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?

Answer: How about just asking, seriously, "Do I make you uncomfortable?"

Question: 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 thought of him as a potential mate but have learned more about him that makes me think we could be 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 stay friends but never know what could have been.

Answer: 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. The damaged friendship is a consequence to weigh carefully. However, 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 friendship anyway. Give it a little time if you want, to give you a chance to read his interest in you.