Dating your best friend. It’s the stuff of romantic teen comedies, and in romantic teen comedies, it always works out in the end (you know, after a big mess in the middle). But we all know life isn’t ever as simple as it is in the movies. So much of a healthy relationship involves a strong friendship, so it’s not uncommon for a person to look over at their bestie and think, “Hey, what if?”
It’s a scenario that’s not unappealing, but is so high risk/high reward that waves of trepidation may discourage the idea. Quantifiably speaking, the pros of dating your best friend tend to outweigh the cons—They already know all your quirks, they’ve already seen you at your worst (and likely have helped you out of it), the trust is there, and most important of all, you like them. But out of the short list of cons, there’s one BIG con. Losing a good friend.
Every friendship is different, but here are a few things to consider if your mind occasionally wanders toward the idea of turning something platonic into something more.
How did the friendship start?
Did you start spending time with this person because of an initial attraction? If so, some of those feelings could still be lingering, and that’s why you can’t get this idea out of your head. If you began spending time with this person because you have mutual interests and are just now noticing what a catch they are after, say, 10 bad Tinder dates, you might just be in a lull that’s clouding your judgment. It’s not that your best friend couldn’t give you what Tinder never has, it’s just that you want to be careful not to date someone just because you think they’re safe or you’re frustrated with dating in general.
What’s the most valuable part of your friendship?
Identifying what’s most important to you in your friendship will help you decide if giving dating a try is worth the risk. If she’s the best drinking buddy you have and your mutual love for the same dive bars are what ties you together, you may decide that a deeper romantic connection is more valuable. If she’s the most constant and stable source of emotional support in your life and you go to her for advice on absolutely everything, the chances of losing her should the worst happen may feel too risky.
What does your friend have in common with people you’ve dated in the past, and what’s different?
Answering this question can be very telling. If you’re always into guys with a sense of humor, and no one can make you laugh harder than your best friend, he may be just what you’re looking for. Alternatively, if you’ve fallen into bad patterns with past significant others, does your best friend mirror or encourage those behaviors, or is he a departure from those types of people? Measuring your bestie up against past loves can give you an idea of what a relationship might be like.
How do you feel about their significant others?
If you’ve always gotten along just dandy with your bestie’s significant others and it doesn’t bother you in the least when they’re with someone else, chances are your feelings are, and always will be, strictly platonic. But if you’re constantly finding fault with the people they’re sweet on (He’s just not good enough, she doesn’t seem to value him, I hate it when he’s with him and not me, etc.), there’s a real chance you’re harboring some deeper feelings.
Why haven’t you dated yet?
Take a good honest look at why, after all this time, you two haven’t gotten together. Maybe one or the both of you were in a relationship when the friendship started. Maybe you’ve felt discouraged because you’re a brunette and he exclusively chases blondes. Maybe you’ve never been turned off by the idea, but there was always someone else who seemed to catch your attention first. If there’s a glaring and immovable obstacle in your way it’s probably best to cherish the friendship for all that it is, and not push for more. If the reason can be chalked up to bad timing or less than ideal circumstances, there’s a chance it could work if both of you are in the right place.
If you’ve considered all there is to consider, and you’ve arrived at that, “I’m gonna go for it!” moment, keep a few things in mind:
1. Your best friend’s honest feelings are as important and as valid as yours.
They may have concerns that you hadn’t considered, or simply may not see you in a romantic light (at least not right away). Asking if they’ve ever thought of you as more than a friend is a safer move than just showing up at their doorstep one day with a dozen roses and your bedroom eyes.
2. Don’t confuse a bruised ego for a broken heart.
If, heaven forbid, you put yourself out there and they’re not into it, it’s going to be okay. You’ll be embarrassed for a while, but keep in mind there is a reason you guys were friends first, and you can remain friends so long as you remember all the things you’ve valued from the very beginning.
3. Keep in mind how the dynamic in a larger group of friends may change.
If you two hop on the dating train, it may shift the vibes in a larger friend group. It shouldn’t discourage you, but just be aware of it. There’s a potential, as there is with any new relationship, that you two may inadvertently seclude yourselves. Make a conscious effort not to let that happen and maybe keep the honeymoon phase PDA to a minimum.