7 Things To Know Before You Start Dating a Friend

The first kiss my boyfriend and I shared as friends-who-now-know-they-like-each-other was nothing short of terrifying. I pulled him into what I thought would be a sweeping, spark-filled smooch and he just stood there, hardly moving. The rest of the date was even more catastrophic. We nervously drank too much and watched Sweet Home Alabama on his bed without looking at each other. I was convinced we had no chemistry and that I ruined a perfectly-great friendship. (Then date two happened and we successfully made out after talking out the awkwardness sh*t storm that was our first date and all was well!).

All to say: I have been there. Sure, friend-to-partner transitions can be magical and simple, but they can also be confusing and anxiety-inducing as all hell if you're someone who doubts themselves a lot. Luckily, there are steps along the way to make this whole process less like the most stressful thing that's ever happened to you. Here are seven things to keep in mind if you're two friends thinking of dating each other:

1. Flirt to test the waters.

It can be tough to suss out if you have mutual feelings when you're already jokey and sweet to each other. “Flirting is a skillful testing of the waters where you’re protecting yourself from rejection," says Dr. Theresa DiDonato, Associate Professor of Psychology at Loyola University. "It can give you a safe space to see if the other person flirts back.”

It doesn't have to be anything too overt right away – we started off with dressing room selfies where we asked each other's opinions on outfits we already knew we looked really good in. Eventually, I graduated to borderline-sexts about how his legs looked in shorts, but there were so many baby thirst steps in between. The point is you can take your time with getting more flirty and seeing if A.) they seem to return the flirtiness and B.) they're flirting with just you instead of generally flirting with everyone.

2. Make sure you have the right kind of friendship for a relationship.

There's a huge difference between your ride-or-die BFF and someone who's just really fun to party with. “I would consider the quality of your friendship before transitioning to a relationship," says Dr. DiDonato. "Do you feel safe and secure in that friendship, or is it an exciting, emotional ride?”

Your friend's robust social life can be hot until they flake on date night over and over again. “Sometimes these dominant traits we love in a person and that drew us in [as friends] becomes the thing we don’t like anymore," adds DiDonato.

3. Be really honest about why you want to date them.

When you've re-downloaded every new dating app only to swear off romance for the rest of your life two hours later, dating a trusted friend can feel like a great option. They're cute, they're nice to you, and you can trust them. But there's so much more to a healthy romantic relationship than just feeling secure.

“There should be some element of sexual attraction or romantic desire," says Dr. DiDonato. "And even if that’s there, there may not be enough for a healthy, stable, romantic partnership.” She also goes on to mention the importance of shared goals and parallel life plans – dating someone who feels "safe" can backfire when you realize they're not as motivated or socially active as you.

4. Go all in if you're going to do this.

Wavering a little is perfectly normal if you both value your friendship and really don't want to mess it up. But consistently worrying about the state of your friendship with every new step you take in your romantic development is just no good.

“A couple who goes through a breakup might then have to negotiate how they’ll share their network of friends, says Dr. DiDonato. "But at the point where they’re a couple, I don’t think it benefits them to keep saying ‘Ok, if we break up, what’s going to happen?’”

Yes, you are taking a risk on your friendship by dating. Yes, depending on if and how you break up, you may not be friends in the end. But if you can't stop focusing on the potential future turmoil, you should rethink moving along. “If you’re both truly interested, there’s more to lose if you don’t try than if you do,” says DiDonato.

5. Don't involve your friends too much in the beginning.

Realizing you might have mutual feelings for a friend can be something you want help sorting through, but if you're going to talk to someone, consider picking someone who isn't a shared friend. “It's not always be a straight path moving from friendship to a romantic relationship – there might be some back-and-forth," says DiDonato. "Shared friends might be really interested in this thing that’s happening between the both of you, but a romantic relationship is between two people.”

Trust: the last thing you need on top of your nerves is a gaggle of mutual friends eyeing you talking to your friend from across the bar and drunkenly blurting out that you should both just kiss already.

6. Expect that things – including sex – might be really awkward at first.

“People bring different sexual expectations to their relationships, so whether you’re expecting magic the first time or you see your sexual relationship as something that can grow and change, that’s going to influence how satisfied you are not just sexually but in the relationship," says Dr. DiDonato. "Two individuals who are willing to work on that factor might have an easier time transitioning into a relationship.”

If your relationship kicks off with a When Harry Met Sally monologue, more power to you. But it's definitely not the standard to hold yourselves to. “If you hold those beliefs, you might take any sort of stumbling as a sign that it’s a problem and this relationship that isn’t worth pursuing, rather than recognizing little points of awkwardness and stumbling as something you can work on,” says Dr. DiDonato.

7. Accept that your relationship will get more complicated.

Just because you get to regularly bone your cool friend now doesn't mean that that's all your relationship will entail. In many ways, things will get more emotionally complex than your friendship ever was, and that's a good thing. “Both people need to be on-board with creating a new sense of interdependence and commitment," says Dr. DiDonato. "It’s not just friends who have a sexual relationship – it’s a romantic partnership. We depend on and our romantic partners depend on us way more than we do as friends."

Figuring out how to deal with jealousy, or meshing your schedules together, or helping each other through bigger life problems you never knew about before are all a part of it. It's not as simple as grabbing a random coffee like you used to. But it's so much better.

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