How to Go About Dating a Friend (and How to Deal With Awkwardness)

Updated 10/11/19
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You only have to cross the line into romantic territory with a friend one time before you realize that the step can ruin your friendship (who else has lost friends because of a scenario like this?). But if it's the right situation, dating a friend can lead to finding your person, which means that taking the risk can be worth it. Plus, since you've spent a good deal of time with this person in a platonic setting, chances are you've already got a good idea about who they really are. "The purity of an initial friendship allows you to see someone's character before it's blurred by sexual intentions and wanting to 'get' something physical out of it," says dating expert Matthew Hussey.

And if you need a little push as to why dating a friend can be ideal, just listen to Wendy Strgar, author of Love that Works: A Guide to Enduring Intimacy. "I extoll the virtues of friendship before dating because you know each other and you have this sense of safety that allows you to explore the relationship more freely," she explains. That being said, there are five key steps you can follow while making the transition from friends to partners that little bit easier. Keep reading to see what experts have to say below.

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Be upfront

While you may try to flirt with your friend subtly to see if they follow suit, it's often best to be forthcoming with your feelings (we know, making yourself vulnerable isn't easy). "I think being honest and direct can save you a lot of grief and agonizing," says love and relationships author Daniel Jones. "I see a lot of stories where people never admit to their feelings and just keep hoping the other person will figure out how they feel, but that can turn into a kind of prolonged torture. Just say it." But that said, don't put pressure on your friend—say you have feelings and then see what they have to say.

Ask yourself the right questions

Why is this person your friend? Is it because they're dependable, loyal, caring and you have shared interests? Or are they the life of the party? Sometimes, we can be friends with individuals who do not make caring partners (going from relationship to relationship or cheating on a partner are warning signs you should stay clear of starting something romantic). "Sometimes these dominant traits we love in a person and that drew us in [as friends] becomes the thing we don't like anymore," says Theresa DiDonato, PhD, associate professor of psychology at Loyola University. Before you try being a couple, really ask yourself Does my friend have the traits I'm looking for in a loving partner?

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Start slow

This is not the time to pick up speed while dating. It will take some time easing into the little things that may seem a little uncomfortable at first. And now's the time to show some restraint with sex (if possible). "Adding sex before establishing that emotional connection makes it hard to go back because you've exposed a degree of vulnerability that can't be reversed, and often becomes a burden," says Strgar.

Keep mutual friends out of it

As with any new relationship, you want to feel like you can talk to your friends about how it's going. But for any small hiccups, confide in someone who doesn't know your new partner—mutual friends will obviously be pulling for the two of you, so their advice will be biased. "It's not always 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."

Don't over-glamorize the relationship

Just because you're coming into this relationship already knowing your partner, that doesn't mean that it's going to be all rainbows and butterflies all the time. Good partnerships require work, so don't go into it thinking you'll be able to put minimal effort in or that there won't be any snags along the way. "There are no shortcuts to doing the work of love," says Strgar. "No partner, even a close friend, is perfect."

Once you've been together for a few months, try one of these fun double date ideas

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