It’s been three months and three dates but you still haven’t gotten that feeling that this date just might be the one. “What am I doing wrong?” you ask yourself. Maybe you’re just too stringent on your criteria. Or maybe you didn’t give yourself a chance to know your dates better and assumed they weren’t for you.

And then one fine day, while you were out having a jog with your best friend, he blurts it out: “I was wondering if it was okay to ask you on a date.”

Initially, you would say, “No way!” But then when you come to think about it, you and your best friend have known each other more than other people do. It’s not a surprise really if you get to fall for each other, but considering a relationship? Now, that would be new for both of you. That’s going to be a game changer, for sure. Do you think it’s worth a try? And if it fails, are you willing to lose your friendship forever? Here are some pros and cons to look into before you decide whether or not you should date your best friend.

The Pros and the Cons

Pro: You can be honest about everything and not be judged.

Con: You know too much about each other.

Knowing too much can include the habits that you tried so hard to keep from your ex that only your best friend knew about. Now the tables are turned and your best friend – who knows your well-kept habits – is your romantic partner! That may lead to fights about pressuring the other to quit the habits. Additionally, there might be trust issues involved.

Pro: You won’t be arguing about which movies to watch or what food to eat because you have a lot in common concerning these things, and if you don’t want the same things, you’ve already been together enough to respect that.

Con: You’ve been so used to doing the same things together that the relationship might run dry.



Being too familiar too early in the relationship might make you feel bored even if you’ve just started dating as boyfriend/girlfriend. If you don’t give each other space, both of you will have a hard time breathing! Some best friends who date are happier when they give time apart from each other. Discovering new hobbies and interests would also help keep the fire burning.

Pro: Most likely, your families love the idea of you dating because they know you and have shared special occasions with you.

Con: There is greater pressure to make the relationship work.

Granny and Grandpa would love to see you together romantically. Mom and dad would feel secure that their daughter is safer with her best friend. You wouldn’t want to disappoint your families, right? But sometimes trying too hard is just what it takes to fail.

Pro: It’s a beautiful story of friendship that developed into love, and what more could someone ask for than ending up getting married to your best friend?

Con: If it doesn’t work, you’ll lose your partner and ultimately your best friend.

That would be the saddest love story ever. All your years of friendship gone because you decided to date your best friend. This is where both you just hope that you really will end up together!

Final Thoughts


Dating your best friend is probably one of the best feelings one can ever experience. Loving, understanding and accepting are easier to do and the respect is less difficult to give. However, despite the benefits of loving your best friend, there is always the tinge of doubt and fear that it won’t last. So before you do jump in and get into the relationship, be ready for whatever the endgame will be.





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