Dear Anna, Hi Anna. I dated a woman for the better part of a year. It was on-again, off-again, and ended shortly before shelter-in-place started, which is when she left...
Dear Anna, About nine months ago, I ended a two-year relationship. We were deeply in love, but we found outside circumstances too much for our relationship to handle. A few...
Dear Anna, I'm one of those weirdos who's on "dating" apps to make friends — I'm single, but not interested in dating right now, only partly because of COVID-19. It...
Dear Anna, I'm 34 years old. I have a friend (girl) who dated this guy (Chris) in high school. At our five-year high school reunion, she finally slept with him....
Dear Anna, I (bi woman, 29) have been having threesomes semiregularly with a married couple I've become quite close with this year. She's bi, mid-30s. Her husband is straight and...
Dear Anna, My boyfriend and I were together for two-and-a-half years. We really loved each other, but for reasons I won't go into here, we didn't work out. I broke...
Dear Anna, My boyfriend and I are about to embark on our first foray into non-monogamy. We've read the books, have discussed rules (like always use protection, no sleepovers and...
Dear Anna, Why would a 63-year-old straight male want to bring a 100% lesbian to his home on the weekends to drink margaritas and stay the night? — No Subject...