Most Helpful Guy
Yes, I would. But only if she is giving me signals, like light flirting, good eye contact, body language showing interest/attraction to me. All these things are indicators that she is either unhappy/unfulfilled in her current relationship or she just can't help noticing other guys (and both are green lights for new guys to proceed). And she would need to be an amazing girl. I'm not talking about nice figure/pretty smile - I'm talking about emotional connection. She has to be someone that attracts me on the inside with personality and HEART (I'm a sucker for super-sweet girls with hearts of gold). If the signals and the emo connection are present, I'm going to talk to her.
I recently took my first shot with a girl in a relationship (I know, I'm old, and you're like, "your first shot, really?"). She had been dating a guy for 1.5 years when we first met. But all the signs were there: Her face lit up with the most beautiful smile when I came around; It was so easy to talk with her; she remembered random facts about me and brought them up in conversations; she had great eye contact with me; she asked me lots of questions to get to know me. Everything about her just screamed PERFECT MATCH and I couldn't get her off my mind, even though I was feeling totally discouraged knowing she already had a guy. But after a few months of chatting with her and wishing and hoping and wondering, I finally decided I had to give it a try. And it paid off. I told her I think she's amazing and that even though she's in a relationship I had to tell her that I like her. She was all smiles and we set up our first date a few weeks ago. On the date she told me she had recently broken up with her boyfriend.