Cleaning Up a Mess... Dating Guilt

iVillage Member
Registered: 05-30-2009
Cleaning Up a Mess... Dating Guilt
Mon, 04-08-2013 - 11:57am

It's been a while since I posted.  I decided to take a dating hiatus after my baby brother's sudden death.  I've slowly been trying to get back into the dating scene (an adventure all its own) and have recently encountered an issue that is in the clean up stages...

First, I haven't had a situation like this since high school, and I am quite surprised to even be facing it now, but it is what it is.  The Dilemma:  my best friend and I like the same guy, and he's interested in me.

To lay some groundwork, here's the deal:  I met this "associate" of my best friend through mutual friends of ours at a party earlier this year.  From the time we met, there seemed to be some chemistry which I decided to quell when she expressed interest in the gentleman.  What I didn't know at the time was that she has known this guy for over 10 years and never expressed any interest in him.  In fact, they never communicated beyond casual conversation at get-togethers.  After this party, I noticed her talking about him and seemingly get excited about him, so I decided to step back and encouraged her to pursue her interest in him.  Over the course of the next few weeks, she communicated to me that she would reach out to him but he never would respond with more than a casual text.  Whenever we would end up at functions together, I would make it a point to make sure they sat together so they could get a chance to interact with each other.  Unfortunately, according to my friend, the guy would never really respond to her "advances" (I use that word because I just recently discovered that she obtained his cell phone number through someone else.  He did not give it to her), so she wrote him off as a "playboy" and I encouraged her to move on...

Here's where it gets sticky.  While at yet another function with our mutual friends (my best friend did not attend), "the guy" and I got a chance to talk and he clearly expressed interest in me.  I turned him down flat and let him know my reason was because my best friend was interested in him.  He seemed shocked, because he never felt like he had given her any indication that he wanted anything more than friendship with her.  I expressed my discomfort with the situation, and he offered to have a conversation with her to clear up any misunderstanding because he wanted to get to know me better.

So... he called her and had a conversation with her (of course I know about this because she called me immediately aftewards--very upset).  A week later, he asked me out again. I decided to meet him for drinks and we really had a great time.  However, I felt so uncomfortable and selfish.  I feel like I am taking something from a friend or doing something behind her back (which I guess I am).  In fact, I felt so bad that I declined an offer for a second date.  The thing is, I really enjoyed spending time with him and would like to go out with him again, but I feel like I should let my friend know what's going on.

...so I'm a little afraid.  Will she get upset with me?  Will she think I vindictively went after this guy knowing that she was interested?  

At the end of the day, the friendship is more important.  How would you handle it?  Until I figure this out, I have not been in communication with the guy.  I think things are too muddy right now.