How To Date Your Best Friend
The transformation from best friends to lovers: it happened in ‘When Harry Met Sally’ and it’s happened to plenty of couples in real life.
It’s rarely easy to cross this threshold though, because there are usually a couple of extra barriers to address.
For starters, one or both parties is usually scared to risk the friendship, so you’ll need to discuss this fear in an intelligent way.
You may also have to jump whatever hurdle prevented you from hooking up in the past.
Ideally, it’s simply because you were never both single at the same time, or she’s only recently blossomed into a hottie. There’s little stopping you transitioning into lovers in these scenarios.
However, if you’ve been attracted to her for a long time, but never made a move, this could be a huge roadblock. If you did make a move and she denied you, that’s potentially even tougher.
Nevertheless, this guide is packed with tips to help turn your best friend into your girlfriend.
There are two types of male/female friendship. A friendship where there is no mutual attraction at all, and a friendship where only one party is harboring feelings.
If you genuinely never used to have romantic feelings, but now do, skip this section.
This section will tell you what to do if you’ve had long-standing feelings for your best friend.
The first question you need to ask yourself is: are you in the friendzone. This term describes the state of affairs where one half of the friendship has firmly decided you’re ‘just friends’.
The friendzone is notoriously difficult to escape. Women, in particular, are very decisive when deciding that certain men aren’t sexual prospects. Nevertheless, it is possible.
Here are the two main reasons why a woman might put you in the friendzone:
So, the first step to winning your best friend’s heart is to stop making these mistakes.
Perhaps she witnesses you making bold moves with another woman. Maybe she spots you standing up for yourself in a non-romantic context.
Either way, she needs to see evidence that you can put the moves on a woman and there is more to you than the classic nice guy.
It’s important to make your feelings clear as soon as possible.
The longer you wait to reveal your feelings, the longer you carry the burden of not telling this important secret to your best friend. This is bound to weigh you down and create a weird vibe.
There’s also more of a risk that she finds someone else – a dude that wasn’t too scared to pull the trigger. Imagine the regret of being too slow to reveal your feelings and some other slimeball getting to sleep with her…
Perhaps most importantly, there’s more of a risk that she sees you as a coward who doesn’t go for what he wants. That’s why it’s best to be vague if she asks how long you’ve been holding these feelings, especially if it’s been for months or years.
You don’t have time to build up the flirting slowly and see how she reacts. That might seem like the ‘safe’ route, but if you’re best friends, you’ve already had plenty of time to lay your cards on the table.
The next time you see her, pull her aside so you’re alone, and tell her you’re attracted to her.
If this was some woman you don’t know that well, you could ask her on a date without an elaborate explanation. In a party environment, you could put the moves on her there and then.
But if she’s your best friend, it’s safe to assume you’ve already been on date-like encounters together, albeit with strictly-assumed boundaries of friendship.
Any unannounced breach of these boundaries is likely to freak her out! That’s why your best move is to verbally state how you feel. Don’t tell her you love her! At the same time, don’t play down your feelings by making jokes about ‘hooking up’. The phrase ‘more than friends’ hits a nice sweet spot in the middle, while making your intentions unmistakably clear.
At this point, you may hope that she’s also been secretly harboring feelings and an epic make-out surfaces out of nowhere. It could happen.
More likely though, she’ll say she needs some time to think, or she’ll default to her objection about only ever seeing you as a friend…
However, that doesn’t necessarily mean that a future romance is completely off the table…
OK, let’s assume so you’ve made a move on your best friend, and she’s responded with anything other than pure positivity.
From here on out, you need to hold your frame.
Your days of platonic friendship are over. There’s no going back. Any attempts to go back will just look weak and submissive, plus you’ll only be going back to a weird icky friendship based on romantic rejection.
So, the right move is to stay strong on the idea of progressing to a relationship.
You may need to continue showing off the masculine qualities that women are attracted to. As unethical as it may be to mention, it’ll help your cause if she finds out about you dating other women. Social proof is a powerful attraction trigger. The more of this she sees, the more she might open up to the idea of dating you.
Plus, the best way to get over the pain of being denied by your crush is to date someone else.
You are risking everything you built by trying to date your best friend. If you were only after a quick fling or some fun in the bedroom, perhaps it’s not worth doing this.
But if you were experiencing a true desire for something more, you need to take that plunge.
It’s no good to be stuck in a ‘friendship’ based on unrequited desire. The healthy friendship was over as soon as you started experiencing these feelings. Being honest about them is always the right thing to do.
So, don’t ever let her shame you for this and never allow her to relegate you back to ‘just friends’. In this moment, you’re either dating or nothing.
If it’s nothing, you need to let that be. Perhaps your friendship can resume when you’re dating someone even better than her.
If the two of you do decide to date, prepare for the possibility of something more magical than the friendship ever was.
About Joe Elvin Joe Elvin travels the world working remotely as a lifestyle writer and confidence coach. Throughout 2017, he filmed his entire dating life as part of a national television documentary in the UK. His new book 'The Camera Never Lies' details the brutal truths about dating and relationships learned from this experience. You can learn more about the book and download the first chapter for free by clicking here >>