Adult Adolescence: 27 And In Love With Your Best Friend's Ex

Just when you thought adolescence was gone for good, that you were now and forever an adult who gets to enjoy all the benefits of adulthood, something tough and hard to handle might happen that throws you right back into adolescence. Adult adolescence refers to the constant process of maturing that can happen at any time in your life — whether you're an 18-year-old entering the world on your own for the first time, a 25-year-old starting to map out the rest of your life, or a divorced 40-year-old who finds himself living the single life again. For over 11 years, I’ve been giving sex and relationship advice to men all over the country to help them lead more successful lives. I’ve experienced the same stages of adult adolescence in my life that you have. Whether it’s looking forward, backward or at what’s happening in your life right now, hopefully I can offer some guidance by examining the difficult times of transition in our lives.

Your 20-something dating life

You are 27 years old and dating. In the six or seven years since you've graduated from college, there have been a lot of ups and downs in your dating life. There have been a lot of crushes, and a lot of times being crushed.

Perhaps your best friend in the entire world was dating an amazing girl, and the whole time they were dating all you kept thinking was: "Why can't I meet somebody like her?" Every time you hung out with them in a group you had such great chemistry with her. She was so cool. You always told your buddy how lucky he was to have a woman like her.

Now they've broken up, and she’s started calling you; she tells you she’s starting to have feelings for you. At the same time, your best friend still talks about her and wonders if he did something wrong.

You’re in love with your best friend's ex, and she is in love with you. How do you handle this? What do you do in this situation?

Dating your best friend’s ex - it’s OK

I am somebody who truly believes that people are not possessions. If I break up with someone — and I have broken up with a lot of people — I have no problem with any of my friends dating my ex, falling in love with her and even marrying her.

This has, in fact, happened to me. My good friend Charlie is married to a woman I used to date. They started dating three years after I broke up with her, and I was perfectly fine with it. So, if you have feelings for your best friend's ex, here is what you need to do: You need to confirm your feelings with her. 
 
Sit down with her and tell her exactly how you feel. You know she feels the same way about you, as you do about her. Have that heart-to-heart talk with her and then ask her: "What do we do about telling my buddy? I don't want to lose my friendship with him, but I do want to act on my feelings for you." Both of you know your friend extremely well, and together you will be able to come up with a way to tell him so that he will not be angry or hurt.

How do you break the news to your buddy? That's next...