Meredith,

I am a 23-year-old single female. Last summer, my friends were up in NH for biker weekend. I stayed home for whatever reason. My best friend texted me and said she had someone she wanted me to meet (we’ll call him Derek). We added each other on Facebook and made plans in July.

By the end of our first meeting, I could read that he was your typical bad boy with a soft side. I liked him. I ended up staying the night, because I did have a little too much to drink, however we did not sleep together. The next morning we went out to breakfast (he paid for us). Some of my friends date his friends, so I thought it was a good fit.

I went home and he went off to work. Any regular guy would text a girl after a good day/night/morning. Nope, not him. I ended up texting him later on that night thanking him for breakfast and trying and get the conversation started. He barely answered. A week went by and nothing. Then he added me on Snapchat. That’s how we kept in contact, by sending stupid selfies back and forth and writing stupid sentences to each other. I was again so confused. He could Snapchat me at work but not text me? Something was off.

Derek is single, no kids, late 20s, shy, outgoing when you get to know him, and funny. I don’t think he’s had a girlfriend in a few years and he’s far from a player. We hung out a few more times but didn’t sleep together. He never pushed for sex. An odd thing to me for someone who is in his late 20s.

We stopped hanging out around October. I still thought about him all the time. One day his best friend (we’ll call him Nick) messaged me on Facebook. I knew this guy had just broken up with his girlfriend, and I was just trying to be a friend. Late in October, Nick threw a party and I went. We ended up fooling around. Nick would continue to text me all day, every day. I started to like him and to forget about Derek. But Derek was always in the back of my mind. I didn’t want him to find out and I didn’t want to be “that girl” who ruins a friendship of over 20 years. Nick agreed but didn’t care, obviously.

Late November, I caught Nick hanging out with his ex so I cut him off. I ended up back at Derek’s apartment a week after Christmas and we ended up hooking up a few times that week. A couple of weeks later, Nick started texting me again. We are both guilty for sexting back and forth. This time I was really upset about it, because I really was beginning to fall for Derek and I didn’t want to hurt him. Nick and I have since stopped the messages.

Derek still has no idea about the relationship I had with Nick. When I was with Derek last week, I felt awful even kissing him. To be that kind of girl going behind his back, with his best friend. I know we aren’t in a relationship, I don’t even know if he has real feelings for me, but it’s just not right and I would never want to jeopardize the future, if there was one to ever come out of this.

I am torn between the two. Will Derek ever come around? Should I come clean to Derek? Based on his personality, I know he will get pissed and probably never talk to me again. Some friends say to drop both and move on. Other say to continue to hang out with Derek.

– Confused