Is It a Good Idea to Date Your Best Friend?

By Michael Fiore
Author of Text The Romance Back

If you want to STOP putting him on the “Friend Zone” and you wanted to know for sure if he is in love with you, you need to watch this video now.

Video: The SEVEN Simple Questions That Prove How He Really Feels

Is It a Good Idea to Date Your Best Friend?

Today we’re going to talk about dating your best friend…

(the “Best Friend” question applies on both sides of the aisle.)

Hannah asks…

“Mike, Is it a good idea to date your best friend? I’ve been friends with this guy for about a year now, he has always said he liked me as more than a friend but at the time I had just come out of a 6 year relationship which began when I was 16, so I wanted to be single and experience dating for a while. Now we have gotten so close, I think I am falling for him. His personality is amazing, he is kind, makes me laugh ALL the time, there for me whenever I need him, I trust him with my life and we always have a lot of fun together. However, I worry that it might be awkward, I am also worried that I might struggle with the physical side, having viewed him as a friend for all this time. I can’t imagine my life without him though. Have you got any advice please?”

    —Hannah

Hey Hannah…

Is it a good idea to date your best friend?

Well, personally *I* would never date my best friend, but that’s mostly because I’m not really into 35-year-old Jewish men and because I think it would really make his wife mad and make my girlfriend go into therapy because she would think she turned me gay.

But let’s change your question around into a couple different questions that I think are worth answering:

1. Is it generally a good idea to date your best friend?

Nope.

“Best Friend” is a pretty powerful and magical position. It’s the person you tell ANYTHING to, the person you know will have your back no matter what, the person who you go crying to when that guy with the abs you met at the coffee stand asks you to have a threesome with him and his work out “friend”.

And it’s generally NOT the person you sleep with, fall in love with or have a REAL relationship with.

The great thing about “Best Friendships” is that they tend to last WAY longer than a lot of “relationships” (especially relationships you have in your early twenties – which, from your picture, seems to be about where you’re at.)

If you decide to date your best friend you have to know 100% that you’re pulling the heart out of that friendship and screwing it up forever just for the possibility that it might turn into something deeper, sexier and more powerful (also, more boring and more critical. Nobody ever picks on their best friend as much as they do their boyfriend.)

2. Can a guy and a girl really be “Best Friends” in the first place?

I get emails all the time asking if guys and girls can be “just friends” or not. And the answer to that one is easy.

YES – as long as that’s all BOTH of them want.

There was some study that came out recently that showed that in male/female friendships the guy tends to drastically overestimate how attracted the girl is to him and the girl tends to drastically underestimate how attracted the guy is to her.

In other words, most of your male “friends” are undoubtedly using you as late night dream material where you wear freaky stripper heels and keep ordering pizza without you even knowing it, even though you think of him as “just a friend” and “more like a brother” than anything else.

Personally, I have quite a few female friends who are just that – friends. That doesn’t mean I don’t find them attractive or that I don’t have the occasional (or frequent) carnal thought about them (some of them are really hot.) It just means that I put them in the friend box long ago and have intention of ever letting them out.

Which brings us to . . .

3. Should YOU Date This Guy…

Sure.

Because he’s not your “best friend” and he never was. And you’re going to lose his “best friendship” soon anyway.

Listen, I know YOU thought this guy was totally 100% OK with just being friends with you. But that’s total and absolute BS. He fell for you – and pretty hard at that – a year ago and has been following you along like a puppy dog ever since trying every damned trick he can think of to get you to wake up to what a great guy he is and that he’s right there in front of you.

And every time you talked to him about some guy you went on a date with or how you wished you could just find a “nice guy” you basically stabbed him in the heart with your sharp, sharp eyelashes.

He NEVER wanted to actually be your friend. He wanted to be your boyfriend. Or at least to get into your pants. And he’s been waiting patiently for you to get over the last guy for a year now, running through every pair of stripper shoes possible in his mind and hoping against hope that someday, just someday he’ll get to feel your soft, soft mouth against his (so romantic.)

So here are your options:

Option 1: Date Him

Sounds to me like you really like the guy and he sounds like a good dude. At this young stage of your life you’ll have the exact same odds of making this relationship work as any other and it’s way better to date somebody you actually enjoy hanging out with than somebody who just sits around talking about WWE all day.

Option 2: Stay “Best Friends”

This will last exactly until you actually start dating somebody else.

Your friendship will become more and more strained as his bitterness wells up in his belly like some kind of alien baby. Eventually, you’ll either have a blow up or will drift apart.

The only chance you’d have to keep the “Friendship” going would be for him to meet somebody else and go absolutely gaga for her in the near future. But at your age, most women he might date are simply not going to be cool with a guy’s “Best Friend” being a perky blonde who he used to have a crush on. So you’re screwed there too.

Option 3: Uhh… There Really Is no Option 3. I Guess You Could Play Video Games Together or Something.

Personally, I think you should date the guy.

As to your other question about the physical side of things: it’s a valid concern but I think you should go for it and find out in the moment. Maybe he’s got some crazy love moves that will make your body hum like a violin.

Tangentially: I’ve been in your position twice in my life. Once in College and once in my early thirties. Both times my “best friend” was a woman who had an unrequited crush on me. And both times the “Best Friendship” blew up in my face and left bitter, bitter ashes. You CAN be friends with guys, but they have to be guys who JUST want to be friends.

And here’s a bonus:

Usha asks…

“Dear Michael,

my boyfriend suddenly stopped talking to me since December last year . After a week I texted him and his reply was “i am fine. busy. will talk to when I can.” Its been 3 months now. Funnily enough we had a good time the last time we met before this happened. he is still on my gmail account but doesn’t respond to my emails or text messages. What do I do ? it’s been 3 months now.

Thanks”

    —Usha

Hey Usha…

He’s not your boyfriend, he’s your ex-boyfriend. And he’s some kind of coward for not just telling you that you broke up. As I always say, the “fade out” and silent treatment is the absolute worst way to end something with someone.

So what do you do? You move on. You delete him from your Gmail. You learn to accept and live with the fact that you might just never know why he disappeared.

Best,

Mike Fiore

P.S. If you want to STOP putting him on the “Friend Zone” and you wanted to know for sure if he is in love with you, you need to watch this video now.

It teaches you the SEVEN Simple Questions that prove how he really feels.