Dear Sasha,

I’ve been seeing this woman for about three months now; she is great in most ways except she’s a huge social climber and will cancel plans at the last moment if she thinks it will advance her social status, both socially and in business. Is this a dating deal breaker? Sincerely,
Is social climbing a […]

Dear Sasha, I’ve been dating this woman that I’m starting to like a lot, the only thing is she has pretty large boobs and goes braless most of the time. I see not only men staring all the time but women as well. Do I say something or not? Sincerely,
 My braless date Dear Braless- […]

Dear Sasha, I have been going to the same gym for a year now and always see the same guy on the treadmill while he’s running, I have a HUGE crush, what is the best way to approach him? I’ve never seen him not running… Sincerely, Crush on running man Dear Crushin’- When it comes […]

Dear Sasha, I got into a fight with my girlfriend and decided not to call her and completely ignored her for an entire week, then that turned into another fight – how long is too long to wait to call after having an argument? Sincerely, How long is too long?

Dear Sasha, I’ve just started dating a new guy that I really like a lot. I’ve had sex with a lot of guys for my age (I’m 25), more than I can count — do I tell him? Sincerely, One too many to count. Dear Too Many- You know what are else too many to […]

Dear Sasha, I dread Valentine’s Day! Last year I had a huge fight with my boyfriend of 3 years the night of and we broke up for the last time of an on again and off again relationship. Honestly I feel like I’ve been traumatized about the day. Just the writing the word makes my […]

Dear Sasha, I met this girl recently online and after a month of seeing her pretty much every weekend and sleeping together, she still won’t introduce me to her friends, she also never talks about them, or her family, for that matter. Do you think that she’s hiding something from me, or just playing her […]

Dear Sasha, Last year my parents got divorced, it came as a huge shock, and no one in the family saw it coming. Since then I have not been able to date (I’m 22.) I get asked out pretty often — but just have no interest. Do you think that my parent’s divorce has made […]

Dear Sasha, I’m feeling really depressed despite the New Year. I broke up with my girlfriend over the holidays. As much as I love her as a person, I knew that our future together was just not in the cards. We each have very, very different life needs and ambitions despite the love. I’m in […]

12-13-10 Dear Sasha, One of my very close friends has a new step-dad who is so amazing and cute. I’m in a spot since I think that he and I have developed strong feelings for each other. (I may even be falling in love!) He has just married my friend’s mom because he got her […]