How Not To Date Your Best Friend

how not to date your best friend

Is it love? Or is it unconditional love?

You’ve been friends with this person for months, maybe years.

Everyone tells you that the two of you are the next Harry and Sally, whatever that means.

You’re attracted to how easy and fun your platonic relationship is with this person.

And yet you still have no idea what to do about it.

Because the question of, “Will this ruin our friendship?” burns in your mind every time the subject is brought up or close to getting brought up.

Most people assume that the woman is always the one to hesitate in this respect, while the man is ready to move the friendship into something more.

This is definitely true in a lot of cases, but men go through the same thought process.

Ladies, I’ve come to believe something depressing: Most guys only want to become your best friend in order to date you.

I know this because I’ve done it, and so has almost every guy I’ve ever met or come in contact with. We talk about it. We don’t like to admit it to you.

Maybe there’s a bright side. Maybe it’s OK to be flattered by the fact that a guy is willing to be friends with you before harassing you with dating requests.

The only problem is that constructs like the friend zone require an immense amount of maturity to navigate, and most guys don’t have the ability to handle that. So for that, ladies, I’m sorry.

But know that even if the guy has an agenda, it can come from good intentions. He’s probably just handling it wrong. He’s attracted to you, but he doesn’t want to quickly ask you out before getting to know you (or he fears rejection…there are plenty of possibilities.)

Let’s be honest. This is borderline manipulative on his part. If the man in the friendship only wants to date you, then you’re in trouble. Every move he makes is going to work toward his advantage first and foremost — instead of yours.

He’ll talk trash about the guys you bring up in conversation (sometimes with clever subtlety), and he may even orchestrate ways to keep you from other friends and possible love interests. For that, ladies, I’m sorry. A lot of us are simply unprepared to handle the responsibility of delicate relationships like this, and human beings are generally terrible at being good to each other as is.

Here’s my story. I’ve always hated the idea of dating your best friend. I’ve never had luck with it, starting with the first time a “best friend” convinced me to stop dating someone else for her (Yes, it works both ways).

Of course, this was back in High School, and that dark four-year time period does a lot of damage to all of us. So much so that it took me years to recover and am still a changed person (she broke up with me a month later). Perhaps for the better.

You’d think I would have learned my lesson, but 5 years after that, the exact situation repeated itself. Best friend + lured me away from another girl = broke up with me a month (and 1 week) later. History repeats itself and all that. Only difference is that we’re still friends years later.

The good news is that these experiences have allowed me to appreciate the close friendships I’ve cultivated with women regardless of whether or not we would end up dating. It’s actually a freedom I wouldn’t dare discontinue.

The best part is that most of you ladies are actually willing to let a guy into your life without having an agenda of your own because most of you understand how a platonic relationship can be just as rewarding as a romantic one.

That’s huge.

But this still doesn’t address the most important problem I see with people who are pressured into dating their best friends. Don’t get me wrong — I firmly believe that growing a romantic relationship from a close friendship is one of the best ways to find someone you can spend the rest of your life with.

We just need to take a step back and examine some things first.

First off, and this is for the men out there, be ridiculously honest. Communicate. If you are attracted to your best friend and you notice the friendship becoming more intimidate, tell the girl how you feel.

It’s scary.

It’s real.

It’s necessary.

If you hold back or ignore your feelings, letting them fester unchecked, then you’re setting yourself up for inevitable pain. The friendship is at actual risk of being ruined when you wait far too long and then drop the “I have feelings for you” bomb. In other words, the longer you wait, the harder and riskier the conversation will be.

The key is to be transparent before you start building a close friendship. If you haven’t asked her out yet because you want to be friends first, then let her know. Let her know that you are attracted to her, but you’re willing to stay friends and be platonic, at least for now. If she isn’t fine with this, she now has a chance to opt out. The same works the other way around.

And if the truth is that you only want to be her friend for the sake of a romantic relationship, then walk away and do some soul-searching. Guys, there is much more to life than seeking a wife, and if that’s all you want from women you aren’t related to, then you need to be single for a while.

So tell the girl how you feel before you let the friendship progress, assuming you have strong feelings in the first place. If it’s basic attraction, you likely don’t need to say anything depending on your maturity level. We’re talking about actual, heart-ready feelings and a craving for true intimacy.

The worst case scenario is that she won’t reciprocate your feelings, but she will hopefully appreciate a clearing of the year. She doesn’t have to wonder what your intentions are. There’s no room for awkwardness anymore because you’ve filled it with a possibility of honest friendship.

At this point, you’ll know exactly where you stand with the other person, and you don’t have to begin pining away for someone who will always see you as a friend and nothing more. You can finally invest healthy emotions into the friendship, which means you both benefit.

Do you know why most friendships end when the guy does tell the girl how he feels? Resentment. Either he will resent the girl for rejecting her when he was so sure she wouldn’t (perhaps because he waited too long), or she will resent him for having an agenda.

This isn’t a science, but don’t wait too long. Prevent resentment by promoting transparency. You can’t resent someone for being honest with you from the beginning.

If she rejects you, then I can almost guarantee that the girl will stay friends with you, and if she doesn’t, it’s fine to move on.

After all, she’s not stupid. She’s likely wondered whether or not you have “other” feelings, and she’s probably waiting for you to just be honest about them.

Ladies, be ridiculously honest. Men can take it. Leading us on for the sake of sparing our short-term emotions can do more damage than you might realize, even if you’re unaware of whether or not you’re leading a man on.

“I’m not ready for a relationship right now.” If you say something to this effect, then the guy (or girl, if the roles are switched) will assume that you will be ready for a relationship with him or her later.

Just be honest. Tell the person you want to be friends. You don’t have to explain it any further. If the guy asks you why you only want to be friends, then say you just want to be friends. You’re not obligated to dissect every emotion you have for the sake of his pride.

That said, handle with care. If the man is willing to talk to you about how he actually, brutally feels, then you’re dealing with someone who is worthy of being your best friend. Why would you want to be confide in someone who doesn’t have the integrity to let you know exactly what the deal is?

Finally, and this is for everyone, you don’t have to date your best friend. You just don’t. Don’t let the pressure from other people and external obligations dictate your personal life.

I think for some of us, we want to date our best friend because we may not be confident in our ability to find compatibility with another human being from the ground up. But do you really believe the odds are against your favor that much?

Give yourself, and the world, a little credit.


21 thoughts on “How Not To Date Your Best Friend

  1. “That said, handle with care. If the man is willing to talk to you about how he actually, brutally feels, then you’re dealing with someone who is worthy of being your best friend.”

    So true. Great wisdom, Jon. Love this!

  2. Jon I loved this article! And, it definitely hit close to home. Having an honest conversation with my best friend on how we feel about each other made our friendship what it is today. I’m thankful we didn’t go the romantic route because my relationship with him doesn’t need that. He gets me, I get him. It’s just great.

  3. Yes – YES. What you described is exactly what happened to me. After 8 years of friendship my best friend came out with feelings I didn’t even know excited &, well, that didn’t end up well.
    For a time, at least. I was best-friend-less for about 6 months after I told him it wouldn’t happens so… there’s that. Your article is excellent, too close home, & I’m sure I’m not the only person in that position.

    I only wish you had written it a couple years earlier,,,

  4. Been in a relationship with my best friend for over 7 years and I just nodded all the way down to the last words, Jon. I’ve been in many “hey bestfriend can you be my girlfriend” situations in the past and everything in this article is suuuper true. Of course I’d say that being in a relationship with your best friend is something really awesome and really special but it’s not that easy too. Everything changes–and that’s one risk you don’t have to take if you’re not 150% ready.

    Thanks for the awesome post, as always, Jon! 🙂

  5. Thank goodness. I’ve been doing it right all along. At least, this time around, I have.

  6. I enjoy your articles, a lot. Your Pixar Theory is so mind boggling and it really makes me think more complex. Your vast view and open perspectives on certain details is so awesome and I think what you do is awesome! -showing love from Missouri, Hailie

  7. I was best friends with this girl for a year, she’d cry with me and I always was there for her, I didn’t mind her flirting with everyone except me and I got it she just was’t into me, but I was attracted to her mainly for who she was and her strong character. After her boyfriend cheated on her for God knows the number of times, she finally left after I counseled her and told her “you can’t let people walk all over you”, and she left him and I was proud of her and not just because maybe I finally had a chance but because I knew she would be free she’d be the girl I knew before. and sure enough eventually we were hanging out almost everyday, not dates but there was a certain tension and I was perfectly fine we we’re both emotionally secure and not really needy people, yea we had nights but whatever flash forward a year she hates me for telling her to change “who she is” and goes back to the same guy as before, (well at least for a month). yea some people make mistakes but others are just stupid.

  8. I Googled “should i date my best friend” because I’m considering a lesbian relationship with a friend who has been flirting with me, and this post was the second result in my Googling. Although some of the advice in this post was helpful, it was difficult to apply to my situation, both because it’s addressed toward men and because it’s addressed toward the more “forward” person in the relationship. Still, thanks for the tips!

  9. Thanks for sharing Jon! You certainly summed up the enormity and complexity of close platonic relationships. It’s a fine balance, a delicate dance that we execute in trying to maintain equilibrium, and sadly one that doesn’t get reassurance from anyone else, other than those committed to the platonic pact. I, too, have been caught between the blurring lines of other people’s dreams for us and our own expectations of ourselves. I have found in time that we have loved each other into understanding ourselves so completely that we probably wouldn’t want to risk the very existence of this happy relationship by doing something as frivolous as trying to change it to something that it could, one day, be but is definitely not, now.

  10. So, guy problem here. My great friend (a guy) told my best friend we were going out. We’re not. I want to know why he did this and ask him, but without coming across mean. Please, oh wise ones (:P)

    • Been looking for advice on this topic for a bit now and this is by far the best article I’ve read on it and really, the only one that I’ve found applicable. We’ve been great friends for years and only recently has the idea of dating become an idea that I’ve given thought to. Every other article assumes the reader to have been madly in love with their friend for years and while yes, that often times is the case, for me I’ve only recently started to see her as potential girlfriend material (despite us having always enjoyed eachothers company, she was never quite the type I look for however, she’s matured into the type of girl I look for and only recently have I realized it) and this level headed approach was exactly what I’ve been looking for. Simple, straightforward and without being dramatic. Thank you!

      • Glad I could be of some help. Sounds like you’re definitely ready to make your decision!

  11. Eugh… I don’t like this at all. I just happened upon this article… Because, yes, I am dating my best friend of sorts and I wondered if other people thought it is equally awesome. Thing is, though, I slowly grew into an attraction of this friend, as did she for me (or so I believe). To manipulate a person’s feelings into friendship for the ulterior motive of sex… Well, that, to me, just seems despicable. Maybe I’m just misinterpreting the MUTUAL INTEREST that is actually present in this here article?

  12. Well,to be sincere,I really enjoyed this article.although I also I had in mind to date my bestfriend.but after Reading this mind blogging article,it changed my desire towards her.and the comments are well couraging.

  13. I know I’m late to the party. Friend of over 15 years told me he wants to know if he has a chance at dating me. His friend asked me “WHYYY don’t you like him”. He got upset that she was putting me on the spot. He was there so my response was, he doesn’t want kids. He then said he does (news to me). I cant meet guys when he’s getting and paying for my drinks and I think his friends think we are dating bc we go out to eat before drinking(?) So, it was probably the beer talking, probably bc I mentioned how I met up with a guy and liked the guy, and probably bc I decided to dress a bit more provocative (bc I was happy I met a guy!). Now I wonder if we need another break. Weve been friends off and on for other reasons. Oh, I didn’t want to be mean so I said, “i don’t know what the future holds”.

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