Dear Annamaria,

Until recently, my best friend at school has been involved in a serious relationship with a guy she’s known since freshman year. I have had feelings for her for a very long time, probably longer than I’ve ever liked anyone before. Although their break-up is recent, she has admitted to thinking that we’d be good together, and I definitely want to act on the feelings I have for her. What is an appropriate amount of time to wait before making a move? How do I avoid being her rebound?

Sincerely, Rebound Rob

Dear Rebound Rob,

Because every break-up and how the persons involved respond to it differs so much from relationship to relationship, there is no easy answer to your question. If being with this girl is what you really want, there are several important factors you need to consider before pursuing her.

First, is taking your relationship to the next level worth jeopardizing your friendship? On the one hand, your friend may return your feelings, and the two of you may become a couple. If this happens and things do not work out, you have just lost the girl you described as your best friend. This is something anyone needs to take into very serious account when contemplating dating a close friend.

An even worse outcome would be for your friend to not return the feelings you have for her. You would be risking your friendship for an unfavorable result. Even if you believe her rejection will not change the nature of your relationship, it inevitably will. You might be able to get past this, but there is no guarantee that your friend will recover from the awkwardness you have brought into your friendship.

At this point, you are probably thinking that, because she has already admitted to thinking that you would be good together, these concerns are not applicable to your situation. Do not be fooled, Rebound Rob. You need to think about the circumstances under which she confessed this. It is possible that your friend was feeling a little sad and lonely about her recent split, especially if she was the one who was dumped. Unfortunately, her self-esteem may be low as an effect of the break-up, and she may have been turning to you, her best friend, for a little comfort. This possibility is especially relevant if her confession came after the consumption of alcohol.

All of this negativity aside, I do not want to discourage you from going after your dream girl. You will need to wait an appropriate amount of time before taking your shot. As best friends, it is implied that you possess a certain emotional connection that will enable you to realize when enough time has passed, when she is feeling like her old self, and when the time will be right. There have been countless successful relationships that began as friendships: Ross and Rachel from Friends, Pam and Jim from The Office, Penny and Leonard from The Big Bang Theory. Yours definitely has the potential to be one too! Best of luck, Rebound Rob!

Sincerely,

Annamaria

Jacq was unavailable this week.