Dear Meredith,

This column has been my savior during bad days at work. I always joked about writing in, but never thought I would. That being said, I think I need your advice. A little background on me: I am in my mid-20s and I’m a chronic dater who would like more than my typical three-to-five date run. I was in a long-term relationship, which I ended, but I have been single for about 1.5 years. I have enjoyed being single but I think I’m ready for something with more substance. I recently met a guy (let’s call him W), who I think I really like. I find him to be very attractive and intelligent, and we have an absolute blast together. He’s exactly what I need right now.

The one little issue is that he spends a lot of time with this girl – let’s call her B. They appear to be very close friends and I had no issue with this in the beginning. I have both male and female friends and understand that friendship doesn’t always lead to sexual attraction. My problem with their relationship is that I sensed that there was some sort of past and I eventually had the courage to ask him about it. Unfortunately, I was right; B and W had a short-term fling where they attempted to take their friendship to the next level. This involved a few months of kissing and eventually led to them sleeping together. W states that the sleeping together only happened one time and that he knew it wasn’t right.

My issue is that I know W will not take B out of his life, and frankly I wouldn’t want to ask him to. I don’t ever want to be the type of person who “forbids” someone from seeing a person; I wouldn’t want someone to do that to me. However, I am not sure I am comfortable with their friendship. I do also need to mention that B and W’s last romantic adventure was only a few months ago, around Christmas. I’d like to think that I can move past it and trust that W’s friendship with B is purely that – friendship. I’ve been single for a while, and the idea of trusting and opening up to someone is a little scary. I don’t want that fear to stop me, but I don’t want to open myself up to a man who potentially still has lingering feelings for someone he sees a few times a month. B and W have mutual friends and hobbies that they enjoy together. W assures me that no feelings exist on his part for B. W does express feelings for me and a desire to continue to grow our relationship. Am I being naïve to think that I can trust him or am I overreacting about his past? I certainly have a long tangled past myself and I feel like I am not in a place to judge. However, I do not see any of my exes on a regular basis. Should I continue to see this guy and see where it goes or is this a glaring red flag?

– Should I run?