Should I Date My Best Friend?

Here we have a question that most of us have asked at least once. What is that fine line between friendship and romance? Is there even a fine line at all? In today’s day and age, the lines in dating are definitely blurred, and unconventional relationships are more the norm, making unconventional relationships more conventional than conventional. Make sense? Not to me either some days, but we are talking about the game of love, so nothing is black and white.

Dating your friend is not exactly an unconventional system however. It’s an age old phenomenon. That being said, it is still today one of the most common dating advice questions in the dating industry. I say, this issue is more black and white than it seems. Here’s why I say that.

When it’s good, it’s very very good, but when it is not, it is ugly.

Does that answer your question?

Here’s the thing. We hear ad nauseum wedding commercials and bridal gushes that this is the most romantic day of their life because they are vowing to their best friend that they will stay with them forever. It’s a nice sentiment, no?

Unfortunately, 50% of those best friends end up in divorce court. And my guess would be that they don’t stay besties when all is said and done and the dotted lines are signed, sealed, and delivered.

So the question is not to be asked of me, the question is to be asked of YOU. Can you afford to lose your best friend?

Sound harsh? Well the truth is that if you go into love and life being realistic, your chances of success are that much better. Nobody wants to start a relationship wondering about the worst case scenario, but if you don’t in this case, you could very well be setting yourself up for disaster.

You want to marry someone that you will one day consider your best friend, right? So it only makes logical sense to us that we consider dating our best friend first, just to see where that goes. And I’m not saying that you shouldn’t do that. What I am saying is, go into this eyes wide open or you run the risk of losing them.

See, here’s the thing. Every time we roll the dice in love we are taking that gamble. We throw our hearts on our sleeves, and dive right in, knowing full well that we might end up heartbroken. But that’s okay, we rationalize to ourselves. All of the gurus and psychologists say that if you don’t put yourself out there, you will never find love at all.


But, when you are dating anybody OTHER than your best friend, you are only taking that one gamble. Or, date your best friend and now you have two really big poker chips on the table. Are you prepared to lose them both?

This is the question you need to ask yourself when you consider dating your best friend. Now that being said, here are some tips that you can sock away in your files of relationship advice should the question ever come up for you in real life. These are some practical things that the two of you can do together to set this relationship up for success.

1. Have The Talk. The only thing is that this talk is going to be a little more intense than your run of the mill dating talk because you are talking to someone that you already love. Someone you may have even loved for years. You don’t know yet if you are in love with them, but you do know how deeply you care for them and that you never want to hurt them. So what differs this talk from others you’ve already had is that you aren’t thinking of yourself. This is the most important thing you need to remember if you take this leap. In previous Talks, you’ve said to your date, “I want more, can we take this to another level?” Or something to that effect.

In this one, your emphasis needs to be on them. “What do you want? What are the issues that you have with this? How can we do this together without wanting to strangle each other?” You have a few advantages when you go to this card game. You have the advantage of history. You have the advantage of already knowing how they deal with conflict. You also have the additional advantage of knowing what hurts them most. This is an advantage so that you can avoid these things all together. So, have this talk, and if you BOTH go into this Eyes Wide Open then you have that much greater chance of success.

2. Have an Out Clause. In your talk, or at some point in your dating experience with them, give each other an Out Clause. “Hey, this is getting weird. I thought I could deal with it, but I can’t. Is it okay if we chill on this for a bit?” The best way to handle the Out Clause is to enter the clause into your agreement when you have The Talk. “okay, I think we can do this, but let’s put something on the table where if it gets too weird for either one of us, we can back out, and still stay besties, no feelings hurt whatsoever.”

It sounds counter productive to establish an Out Clause, but consider this the emotional prenuptial agreement you both come to. Why? Because you both already love each other. If pain enters this relationship at any stage, it is going to hurt one hundred times more than if you were dating Average Joe from the tapas bar down the street. Give both of you this out clause, then this releases some of the pressure. And, it gives you both a bit of an emotional insurance policy so to speak. That insurance policy to comfort both of you in the notion that no matter what happens, you will still be besties.

3. Have an open no holds barred conversation about sex. Did it ever occur to you that your best friend might one day see all your naked tiddly bits? If not, you need to start thinking about that. For some, this is enough to stop them in the tracks of even starting. Again, I’m not suggesting you don’t do this, just have your eyes wide open before your eyes open wide over something you just…weren’t expecting. I’ve seen bestie couples reach this stage and have that awkward moment that is not unlike accidentally walking into your mom when she’s showering. You could be as excited about the prospect as anyone would be to sleep with your bestie, but you don’t know the potential weird factor until it actually happens. There might never be a weird moment for either of you, and to those couples I shout, BRAVO. But thinking about this before it happens will help prepare you.

Now, look at the flip side. This person already loves you. So, you don’t have to feel so self conscious about this first time. If the chemistry between you is out of this world, you can and probably will have an outstanding sex life right from the hop. Because you love each other deeply and this takes away all of those inhibitions right from the very beginning. That’s the beautiful thing about this kind of relationship, it is comfortable right from the get go. So all I am saying is, prepare yourself beforehand.

There’s nothing like having a best friend. Nothing like it in the world. But there’s also nothing worse than losing one. So when you take this to a dating level, you just need to be a little forewarned, and prepared, for the potential pitfalls. This kind of dating experience requires a little more relationship advice than the average couple. In that same vein, you have a much better head start than the average couple, because that love and trust is already established.

Like I said, when it’s good, it’s very VERY good.

But when it’s not, well, then you are out a best friend and wishing you could turn back time and not ever make that mistake again. Forewarned is forearmed. Be prepared, and remember who you are dating. Put their needs first, and make sure they are doing the same, and then I would love to see you two….invite us to your wedding.