The obvious answer typically would be the bad boy, the bum, or the player, but those guys aren’t the ones that I’m talking about. You should already know that by now. The answer is simple. From my own experience, I believe you should never ever, and I mean never ever, date your best friend. I don’t mean you and your boyfriend now have become best friends. I’m talking about someone you are currently best friends with now. Now some of you may be reading this like, “Duh, girlfriend, what were you thinking?” Some of you may even be disgusted at the thought of being romantically involved with your best friend. Good. Keep it that way. Other than that, there may be a few of you who it actually worked out for and I bet I know the reason why.
The only way dating your best friend will work is if the guy has secretly been in love with you since the day he met you. Look at Ross and Rachel from F.R.I.E.N.D.S. The fact that he was in love with her may not have been so secretive, but when Rachel figured it out, all of the sudden it clicked and she fell for him too. Only problem was it took them 10 years to finally stay together, but they were made for each other nonetheless. A similar situation exists in the film, Just Friends with Ryan Reynolds and Amy Smart. Growing up, he was overweight and secretly in love with her but she didn’t consider making him her boyfriend until their reunion years later. It worked because he always had feelings for her and then she was the one who finally came around. Not to sound completely pessimistic, but notice how both of my success stories aren’t real.
Unfortunately, this will not work if the situation is reversed and you secretly have had a crush on him. The fact that he thinks you’re pretty or tells you that you look good in your favorite dress doesn’t mean he has feelings for you. Also, when you complain to him about other guys and he tells you they’re jerks and you deserve better doesn’t necessarily mean he’s referring to himself. Don’t get confused. Maybe one night the both of you had a few drinks and you kiss. It felt weird but amazing at the same time. Stop there. Even if you both agree that you will either really try to make your relationship work or are strictly going to turn into friends with benefits, they both will blow up in your face. Having a romantic relationship with your best friend for a short amount of time is not worth losing that person forever afterward. Again, the two of you may agree that no matter what happens you’ll always be friends. That becomes complicated when one of you gets hurt or finds another significant other. Now you can’t talk to each other at all and your days of jokes and good times are over.
If you were supposed to be in a relationship it would’ve happened a lot sooner than later. The biggest issue with shifting from best friends to boyfriend and girlfriend is someone doesn’t know how to flip the switch. The two of you used to hang out all the time without having to hold hands, kiss, or show affection at all. When it becomes public it can almost feel forced or awkward. For those of you that are currently in this position, I don’t mean to condemn your relationship. Just consider this as a friendly warning.