Dear Gems from Jen,

My best friend of over 10 years recently broke up with her boyfriend of four years. When she called to talk to me about it, she explained that one of the main reasons that they broke up was because she started thinking about what their future together would be like and realized that they had irreconcilable differences when it came to religion and spirituality (namely that he wasn’t Jewish). She went on to tell me that she wanted to be single and see what was out there and maybe find a nice Jewish guy that spoke Hebrew. The conversation got me thinking and I started hoping that I was that guy.

There was a time when we first met that I was in love with her. Nothing ever came of it, but I have loved her as a friend for as long as I’ve known her. She’s smart, has an amazing smile, loves music and there isn’t a woman that I’ve dated since we’ve known each other that I didn’t compare to her in some way or another. I’m getting older and I feel like my window of opportunity is shrinking, but I wonder if it’s worth it.

In my heart, telling her how I feel seems like the right thing to do. I know it’s selfish and I know that she still has feelings for her ex, but I don’t want to live my life regretting not taking that chance. We don’t live in the same city and I’m thinking about visiting soon and telling her what’s on my mind. Do these ‘best friend professes love’ situations ever pan out or am I just a fool in love?

Please help.

M in Love

Dear M in Love,

I believe that one of the most important components of a relationship is the best friend piece. Now, does that mean this will ultimately work in the way you are hoping? I sure hope so, but I can’t be sure. You have a lot to think about here. Are you willing to risk this friendship if she does not reciprocate your feelings? In my experience, it can become awkward when a friend professes love. When it has happened in my life I usually saw it coming, but for the most part, I haven’t been on the other end of the situation. However, this is my experience and her feelings may be exactly what you are hoping for.

Secondly, if things do go your way, what happens if the relationship does not last? Changing the dynamic of a friendship does tend to change everything. Is your friendship strong enough to bounce back from a romantic relationship if for some reason it does not work out?

Why is it selfish for you to be honest about your feelings? Also consider the timing of your revelation. Perhaps letting her have some more time to move on from her ex might make both of you feel more comfortable. If you chose to tell her how you really feel, don’t wait too long.  The longer you take the more difficult it will become. Most people tend to over analyze the situation, which creates unnecessary anxiety.

My next question; if you have always had these feelings why have you held back for all these years? You never know, she could have these same feelings and is waiting for a sign from you. Living life with regrets is really no way to live. I cannot make you any promises, but I don’t want you to look back at this moment years from now and have thoughts of “what if…” Sometimes the risk is worth the potential fall.

Gems from Jen