Ashley (lupinlover) wrote in thequestionclub,

yay dating question

I'm interested in a much older, single man (yeah I know stay away) and I'm pretty sure he's interested in me (he's always flirting, asking me questions about myself, seems genuinely interested), but he hasn't asked me out. Is this the sort of situation where I'm probably just going to ask him out due to the "older man/lolita" stigma?

additional info: we work together (bad, I know) but we're peers (he's not my boss or anything) and there aren't any rules against dating cowokers. He's 18 years older. I'm 21, he's 39. Like I said he's always flirting with me and/or asking me questions. He'll ask me hwo I'm doing every day, how school is going, how my family is, friends are, he remembers everything I tell him and then follows-up with more questions about all of that. Plus he's complimented me on my looks many times.
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