There’s a woman that I really like and can't stop thinking about. We’ve been friends for five years; we worked together but I was married at the time. I think she felt the same way. We were always very flirty with each other and she used to say things like “too bad you're married.” We would go out for drinks, lunches, and work parties together because my wife never wanted to come. We kissed once at the Christmas party but as soon as we realized what we did, we promised to never let it happen again.
I moved to another state for my wife’s job but soon after she decided she didn’t love me anymore and we divorced at the beginning of this year. I moved back home and I feel ready to date again. This woman I like is with someone else now and it's pretty serious. We are still very flirty when we're together and I think she knows I want to be more than friends with her. Should I risk wrecking our friendship by telling her, or do I wait to see if the relationship she’s in works out? — Unsure Sean
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Dear Unsure Sean,
There is clearly a connection between you and this woman so instead of passing up an opportunity to be with her, I think you should tell her how you feel. Sure, it's a risk to your friendship, but there's always been an underlying attraction there so I'd say that you've always been a little more than friends anyway. If you're worried about her reaction, stipulate your admission by telling her you're not necessarily looking for an answer from her, rather you needed to be honest with your feelings. If all goes well, you'll be glad you put your heart on the line. If she doesn't reciprocate your interest, do whatever you can to not let your talk affect your friendship. If I was a betting women, I'd say you two are on the same page so my advice is to just go for it — you'll never know unless you try!