7 Mindblowing Reasons Why You Should Be Dating Your Best Friend

Do you find that your relationships fizzle out once the 3-month mark hits? You chase relationships with guys you have NOTHING in common with. It’s keeping you single and stopping you from settling down in a relationship. What’s the problem? What gives?

In fact, you might be overlooking an all-too-obvious resource: your male best friend. If you haven’t considered dating your best friend, this article will give you reasons to look at him in a new light.

A Caveat

Before you get excited and think you’ve found a cure for your lonely heart blues, let me just say: you can’t force chemistry. Yes, you are already compatible with your best friend, but that doesn’t automatically mean you’re romantically meant for one another.

On the other hand, the thought of having romantic feelings for a man you’ve known for years but have only considered a friend might be a little jarring. You might think of him as a brother and couldn’t possibly imagine kissing him, let alone…

All I’m asking is that you just be open to the possibility of romance if you have a close male friend who is single and amazing!

Why Dating Your Best Friend is a Wonderful Idea

You’ve gone out with total strangers and haven’t felt like you could open up to them the way you do a close friend. Obviously you feel a connection with this man and are comfortable with him, so here are some reasons you might need to reframe how you see him.

1. You Already Trust Him

Trust is a HUGE thing in relationships, and it’s something that has to be earned by both people over time. It’s also important in friendships, but, if this man is your best friend, you’ve already built that bridge.  The two types of trust are a little different.

Trust in a relationship can be harder to win because you aren’t sure at the start of a relationship if a person is being genuine or who he thinks you want him to be. For example, maybe he is always on time and plans all the dates you have together at first to win your heart, but later, his lazy nature comes out and he starts being late.

A friendship, on the other hand, has less to prove. Your male friend isn’t trying to get you to fall for him, so he’s more likely to be himself and earn your trust that way. Because you already trust him, this is a great foundation for an honest and real relationship. The fact that 40% of couples in a research study were friends before they started dating is a testament to the power of trust in a relationship.

2. He’s Completely Himself Around You (and Vice Versa)

Another perk of friendship is that you have no reason not to be yourself. If you were dating a man, you might not burp, snort through your nose, or wear your lucky green hat to every football game. But with your friend? Why the hell not? You’re not trying to impress him, and the more comfortable you can be around him, the better the friendship.

You’re completely cool with the fact that he walks around in ancient pj pants when you come over to play Rock Band, that his house is perpetually dirty, and that he talks with his mouth open. You might even find these traits endearing because you already love him as a friend. If you were dating a new guy with these habits, it might be harder for you to look past them to find the good stuff.

3. He Knows Your Stories, Both Good and Bad

Getting to know someone while dating is part of the fun, but it’s also tedious if you’re telling your stories over and over again. Telling a man about your nasty divorce? Not fun. Explaining for the billionth time what you do for a living? Meh. But dating your best friend requires none of that. He was there when it happened. He held your hand and wiped your snotty nose as you cried on his shoulder.

And you were there when he got his promotion at work. You were cheering him on through the good and ready to listen with the bad.

What more could you want in a partner?

4. Dating Will Feel Natural

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Admittedly, it might seem a little odd at first when you start dating your best friend because you’ll have to transition from acting like friends. But the transition won’t be as hard as you might think. You won’t be a wreck trying to figure out what to wear for your first date. In reality, you’ve been on dozens of dates with him…you just didn’t know they were dates!

Because you’re already so comfortable around one another, a date should feel like a natural extension of your relationship.

5. He’s Already Met Your Family and Friends

Introducing a man to friends and family can be nerve-wracking. Will they like him? Will they think you’re good together? Would they tell you if they didn’t?

Because your best friend already knows most of the people you care about, this is something you can check off your list. You’d already know if anyone you cared about didn’t like him, so you can assume you have everyone’s approval to date him.

6. You Know What He’s Looking For

Ugg, the dreaded DTR conversation (that’s Define the Relationship if you didn’t know). It can kill what otherwise seemed to be going well when you’ve been dating a man a few weeks. This has historically been when you let him know that you’re looking for commitment…and he told you that he was just looking for something casual.

Only, with dating your best friend, you already know what he wants. You know that he’s been hoping to meet a woman he could commit to and spoil for life (you’re like, “sign me up!”). So you don’t need to stress about having that DTR conversation. You know you’re aligned in what you want.

7. You Have Things in Common

It’s hard to find someone you have things in common with later in life, particularly if you’re meeting men on dating apps. You can only get to know someone so well with the brief bio they fill out.

But you’re friends with this guy because you have things in common. Maybe you both love a particular hockey team or enjoy painting together on the weekends. There are already some common points of interest, which paves the way for a fulfilling relationship.

Reasons to Think Twice Before Dating Your Best Friend

So, all that being said about why dating your best friend might be a good idea, you might still have some hesitations. As well you should: shifting from being friends to being in a relationship will definitely change things…and you might not be ready to do that.

You Worry It Will Ruin the Friendship

Sadly, just because this man is your best friend doesn’t automatically guarantee that you’ll fall in love and live happily ever after. You may have a slightly better chance of making it than you would with a random guy, but you need to consider what will happen should you break up. Can your friendship handle it? It’s rare that friends who date and then break up ever go back to being as close of friends again. Are you willing to risk the friendship in the hope that you will make it long-term as a couple?

You’re Looking for Different Things

You might have a fantasy of marrying your best friend and are overlooking one major fact: he in no way is ready to settle down. When you have love blinders on, you can end up getting hurt if you both want different things in a relationship.

This is one reason you shouldn’t have sex with your friend unless you’ve decided to be in a relationship. He might assume you’re doing the friends with benefits thing…while you’re trying to connect with him emotionally. If you have feelings for him, have a conversation about it so you don’t end up with hurt feelings.

If You Do Start Dating Your Best Friend…

If, after reading this far, you’re ready to jump in with both feet and start dating your best friend, make sure you go about it mindfully.

Realize That the Dynamic Will Change. Discuss It.

It might seem like things will stay completely the same once you start dating, but there will be fundamental changes. Where you spent a lot of time together as friends, you might need some space now. You will likely have different expectations of one another. Talk upfront about how things will change so it’s not a surprise.

Be Prepared to Answer Questions from Curious Friends

Just ask Rachel and Ross or Chandler and Monica: a group of friends who know you as BFFs one day and then lovers the next will need a little time to adjust to the new dynamic. They may have opinions—no, in fact, they will have opinions. And questions. So maybe wait to announce that you’re dating until you’re prepared for the barrage of questions. If you’re just trying to figure out your feelings for one another, you might not want to make a big announcement just yet.

Keep Communication Lines Open

Despite being able to talk about everything as friends, you might find yourself shy or insecure about telling him certain things now that you’re dating. Just remember: you know and trust this guy. You can tell him anything. Make a point to do regular check-ins to see how you’re both feeling about the situation. Express any concerns or needs you have that aren’t being met.

Go Slow as if You Didn’t Know Each Other

While it’s wonderful that you don’t have to start from scratch in getting to know this man as you begin dating, in some ways, you should pretend that you’re strangers. With sex in particular. This is a whole new world to explore together, but make sure you’ve sorted out your feelings for one another before you jump into bed. You want to make sure you’ve both agreed to commit to one another…otherwise you end up in that friends with benefits situation I mentioned earlier.

Conclusion:

Dating your best friend has so many benefits. It’s pretty amazing to one day look at the man you’ve considered your closest confidant and see him as an attractive, intelligent man that you want to get to know on a whole other level. Enjoy it. Being in a relationship will enhance your friendship like nothing else.