Dating Your Best Friend: Reasons For and Against

Sometimes it just happens. You have known your best friend for years and one day, out of the blue, you start seeing that person in a different light. For reasons that no human being will probably ever be able to understand, you have become strongly attracted to your best friend. You probably never expected it to happen, but there it is, and there doesn’t seem to be any way to fight it or talk yourself out of it. It has hit you like a ton bricks and you had hoped that it was just a “phase” that you were going through and that it would pass with a little time. That didn’t happen.

So, now what? Do you pursue this and tell your friend about it or do you continue to suffer in silence? It’s decision time and it will probably be helpful for you to be aware of the following good reasons for you to open up and let your feelings pour out. On the other hand, there are a few good reasons that you should keep this to yourself forever and hope you can just get over it. It may be one of the most difficult decisions of your life, but it’s not one your heart will let you ignore. One way or another, you will have to decide.

1. Pro: No wardrobe stress

Chances are good that your best friend has already seen you when you are a long way from being dressed to kill. They have also probably seen you when you are looking your best as you head out for a night on the town. You have an already-established level of comfort with your best friend that should eliminate the stressful experience of struggling to pick out the outfit that will make you look your flawless best.

2. Con: You’re a little too comfortable

Your best-friend-turned-lover has likely already seen you in your hanging-out-at-home-watching-TV-on-a-Sunday-night outfit so what’s there to hide, right? Why not throw on a pair of old sweatpants, a t-shirt, and well-worn sneakers the next time you two go out to do something? Well, for one thing, taking a relationship beyond the friend zone may cause you to look at one another in a different light. While hanging out with a friend who looks like a hobo might be cool, there will often be new and different expectations when that person becomes a serious love interest.

3: Pro: No first date discomfort

There’s no question about it. That first date with a potential new love interest can be a gut-wrenching, anxiety-fueled experience. Sure, breaking the news to your best friend that you want to be more than just friends can be a bit nerve-wracking, but at least you don’t have to get through that whole awkward getting-to-know-you phase of a relationship. And since you have been hanging around together for a while already, selecting that first date activity or location should be a cinch.

4. Con: Your first date feels like just another night out

Even though you and your best friend have probably known each other for a good while and have spent a lot of time hanging out, that first time you get together to do something as a couple should feel different. In many ways, it should feel like a first date without all the getting-to-know-you awkwardness. If that isn’t the case and it feels like you are just spending time chilling with your bestie, it could be a sign that you two are better off just being friends after all.

5. Pro: No family surprises

Whether you like it or not, your significant other’s family is going to be a part of your life and in many cases, they become a very big part of your life. Since the chances are pretty good that you have already met and gotten to know your best friend’s family at least a bit, the likelihood of nasty surprised is lessened. Relatives and the problems that sometimes go along with them have been the cause for more than a few break-ups.

6. Con: You know the family and wish you didn’t

If your best friend’s folks are the ones you’d most dread being stranded on a desert island without of all the people in the known universe, your best choice might be to just ride out those feelings you have for your best friend and hope they fade away with the passage of time. That really does happen for some people and they often find themselves at a loss to explain how an attraction like that could have ever have developed once they look back on the whole experience a few months or years down the road.

7. Pro: You already have the same friends

Perhaps there’s not complete overlap where you and your best friend’s friends are concerned but chances are pretty good that you have a few friends in common. That should at least somewhat reduce the chances that you are going to clash with their friends if you take your relationship with your best friend to the next level.

8. Con: Losing friends after a break-up

Break-ups happen all the time and as perfect as any romantic relationship seems from the start, there’s no guarantee that it will hold together in the long run. With many of the same friends, it’s not unlikely that some of them will go one way and some of them will go the other way in the event of a break-up. Not all friends feel like they need to pick a side when things like this happen but it is not uncommon.

9. Pro: They have already seen the worst of you

Chances are that you have already spent a lot of time with your best friend. You’ve gone places and done things and have spent hours just hanging out talking about anything and everything. You have probably even had a few good fights, but you always makeup and pick up where you left off. This person probably knows you better than almost anyone else. They know your secrets and they have probably seen you at your worst.

10. Con: You already know about their flaws and you can’t get past them

With a friend it might be a bit annoying that they constantly interrupt your conversations to answer a text message or chew their food with their mouth open, but could you stand these flaws being part of your relationship with your significant other?

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