I am currently friends, and I use that term somewhat loosely, with two men that I once dated. We are not the best of friends, for sure, mostly just the occasional interaction on Facebook. And in both cases, we realized we were better as friends. And one of them we only recently got back in touch after many years of not talking.

With both men, however, there was a time when we were much closer friends. And for both, our friendship was stronger after breaking up romantically. But it doesn’t always work out that way when you decide to date a friend.

Many people hesitate to date a friend out of fear of ruining the friendship. They worry that if it doesn’t work out, they’ve not only lost a romantic partner but a good friend. It’s a valid concern, but there is another side to it.

What if it works out? If it works out, you end up in a relationship with a very solid foundation of friendship. You could end up in a relationship that is stronger, and longer lasting, than the average because you were friends first.

It’s the fact that we don’t have a crystal ball to see the future and know which way things will go that makes us hesitate. We want to try for the long, strong relationship but we don’t want to risk the friendship. So instead, we teeter on top of that fence between the two, trying to decide which way to fall.

If you’re teetering on that fence, consider the following.

Just because it didn’t work with one friend doesn’t mean it never works

Sometimes we hesitate because we’ve dated a friend before, it didn’t work out, and the friendship was ruined. We assume from that experience that this is how it’s doomed to be whenever friends try to date.

But that’s not necessarily true. Ask around. You’ll probably find at least one couple among your friends who were friends with each other before they started dating and/or got married. You’ll probably find more friends that can tell you about friends of theirs who have done it.

So don’t assume that just because you dated one friend and it ended in disaster means history will repeat itself if you date another friend. Maybe the first friend just wasn’t right for you as a romantic partner and the second friend is the person you’ve been looking for all your life.

It can be awkward at first (really awkward)

Transitioning from being just friends to being in a romantic relationship can be really awkward, at least in the beginning. In many ways, things really aren’t that different and yet, everything is different.

Many of your conversations are the same as what you had when you were friends. Dates can easily feel like you’re just hanging out with a good friend. Sometimes you might even question whether you’re actually dating your friend or not because it really doesn’t feel so different.

But that first kiss, not to mention the first time you have sex, can feel really awkward.

Just because it feels awkward as you navigate the changing status of your relationship doesn’t mean it’s not working. It just means you need to be patient and allow both of you time to adjust. If you’re open to allowing the awkwardness to just be and to go away on its own, you’ll quickly see what’s awkwardness and what’s not working.

You need to be clear on the potential outcomes

Dating a friend has about four ways it can turn out:

· You date, it works out, and you live happily ever after

· You date, it doesn’t work out with a horrific breakup, and your friendship is ruined

· You date, it doesn’t work out with a moderately uncomfortable breakup, and you go through a period of awkwardness as you readjust to being friends

· You date, it doesn’t work out, but you both realize it and your friendship is unaffected

It’s important that you recognize these possibilities, and that others may exist, before you make the leap to date a friend. It’s important that you not just recognize them, but understand that any one of them can be the one that happens to you and your friend.

If any one of them (specifically, that the friendship is ruined) is absolutely unacceptable to you, then you should think very carefully before moving forward with the idea of dating your friend. If you can’t stand the thought of losing your friend as a friend, or of there being some awkwardness or discomfort, dating a friend might be a risk you don’t really want to take.

You need to be extra clear in communication

The foundation of friendship can lull you into thinking that your friend should know exactly what you want from them when you’re dating — but that’s not necessarily the case. They know you as a friend and vice versa. You can’t make any assumptions about what either of you want in a relationship.

You need to be extra clear in communicating your wants, needs, thoughts, and feelings when you date a friend. Don’t make jokes, give subtle hints, or hope they read your mind. Be straightforward and honest about your expectations and what you are and aren’t getting from the relationship.

You also need to be more alert to asking your partner about their wants, needs, thoughts, and feelings. Even when you are making efforts to be more clear, they may not be. So check in with them and make sure that you understand how they feel, what they want or need from you, and what they are or aren’t getting.

Clicking as friends doesn’t mean you click as a couple

As I learned from the two friends I once dated, sometimes you can be absolutely outstanding as friends but absolutely suck as a couple. The simple fact is what makes you click as friends isn’t always the same stuff that makes you click with someone romantically. If that were true, we’d all be in love with all our friends all the time.

You know your friend pretty well, so take some time to assess them objectively as you can. What do you know about them that matches up with the kind of people you typically date? Or if you’re wanting to date a friend because you think they’re a better choice than past partners, what makes them different?

Write down what makes you connect as friends and then consider whether the things on that list are the same things that you look for in a partner. If they’re not, consider what it is that makes you want to date them.

It can go wrong and that will change your friendship

There are friends who date, mutually realize that it’s not working, break up and return to being friends with only some mild awkwardness and discomfort or none at all. And then there are friends who date with disastrous results and end up with a friendship that is completely destroyed or at least changed significantly.

If you’re in the first group, where you can mutually realize it’s not working, your friendship will probably be largely unaffected. Even if it’s only one partner who realizes it’s not working, if the other is able to accept that, it can still work out okay.

But if you end up in the second group, where it all goes wrong and sometimes in truly catastrophic ways, you need to know that it will change your friendship. And it might be a change that you can never fully recover from.

You might end up being Facebook friends but never speaking to each other. Or you might still call each other friend but only see each other when you get together with a group of mutual friends.

It’s this change that makes the next section even more important.

Be brutally honest about how things are going (including ending things)

When you’re dating a friend, it’s easy to try to persuade yourself that things are good. That if you just give it enough time, the problems you see will resolve themselves. That you need to be patient, or loving, or your expectations are too high, or… there are tons of excuses you can make.

But the longer you drag things out when it’s clearly not going well, the more damage is being done to your friendship. You might think you’re saving the friendship, or softening the blow to your partner’s feelings, but you’re actually making it worse for both.

While you need to allow for the initial awkwardness to pass, you also need to be brutally honest with yourself and your friend about whether the relationship is working or not. And if it’s not working, it’s better to end it sooner rather than later.

Your friendship stands a much better chance of surviving if you do this than if you try to make excuses and force a romantic relationship that clearly isn’t working.

Consider their past relationships

Before you take the leap to try to date a friend, think about their past relationships. Have you seen them in a relationship before? How did it go? How did it end? How did they treat their partner?

It’s true that you only had an outsider’s perspective on their relationship, but if what you saw wasn’t what you’d want others to see of a relationship you’re in, you probably don’t want to date your friend — not that one, anyway.

And if they haven’t had any relationships? Or none that lasted long enough for you to ever meet the person they were dating? Those should be red flags that dating them isn’t a good idea. Not only is the relationship unlikely to work out, but you might end up losing all respect for your friend once you learn how they are in a relationship.

Dating a friend can, and many times does, work for a lot of people. The fact that sometimes it doesn’t work shouldn’t deter you from trying if it’s what both you and your friend want. You just need to be sure that you’re going in with eyes wide open and fully understanding the potential consequences to your friendship.

Wendy Miller is a Certified Happiness Coach, freelance writer & meditation teacher. After years of settling for abusive and otherwise toxic relationships, she got fed up. Using meditation and other tools, she got to work on healing herself, setting boundaries, and only engaging in relationships (romantic and otherwise) that bring her joy. She wants to help other single parents find the love & happiness they seek, including and going beyond romantic love. She lives in Florida with her two sons, where she homeschools while solo parenting, while surrounded by what feels like a zooful of animals.

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