How to Transition from Just Friends to Dating—an Expert Weighs In

Friends to Dating
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It's no secret that falling in love is easy. In fact, some might argue that it's the simplest part of a relationship. The commitment, compatibility, and trust are what tend to be more difficult to manage, especially if the one you've fallen for happens to already be a close friend.

"Catching feelings for your BFF happens. The happily ever after party? That happens mostly in rom-coms," Darcy Sterling, Tinder's dating and relationship trends expert says, point-blank.

It's not impossible to transition from just friends to dating; however, Sterling recommends you do your due diligence before professing any feelings and risking the special friendship you already have. "It's important to realize that the minute you put your feelings out there, you cross the Rubicon," she says.

Meet the Expert

Dr. Darcy Sterling is a Licensed Clinical Social Worker and the star of E! Network’s hit show Famously Single. Darcy and her wife, Stephanie Sterling, share a New York City practice called Alternatives Counseling.

If you've already done some serious soul searching and decide that it's worth it to pursue a romantic relationship with a friend, Darcy points out that communication will be the key to the potentially awkward transitional period.

Curious to learn exactly how Darcy would approach getting out of the friend zone? Ahead, she explains how to know the relationship is worth chasing after and how to move on once you've put your feelings out there—for better or for worse.

Ask Yourself the Real Questions

Relationship Questions
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Darcy's first piece of advice for making a friendship something more is to think long and hard about the decision (something you've likely already spent a good amount of time doing). To help you make your daydreams a bit more productive, she poses a few enlightening questions to ask yourself in order to figure out if the risk is worth the reward (or potential heartbreak). 

First, there are the basic, logistical questions to consider. Are you both single and of the same sexual orientation? Are you both looking for the same kind of relationship status? According to Darcy, if the answer to either of these questions is no, she doesn't think it's worth the risk. "Relationships are hard enough to maintain when people are compatible," she points out. And you're likely going to ruin what friendship you already have by attempting to change the game under these circumstances.

Relationships are hard enough to maintain when people are compatible.

If you are both single, of the same sexual orientation, and looking for the same kind of relationship (serious, open, or otherwise), Darcy suggests asking yourself a few deeper questions. Think to yourself: How likely are they to have feelings for me? What's the cost of keeping your feelings to yourself? Can you truly continue being friends if they don't feel the same way?

Look for Signs of Flirting

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When it comes to getting an idea of whether or not your friend may also be interested in taking things to the next level, there are a few indicators you can look for. "We humans aren't great at hiding our feelings," Darcy says. "We flirt. We touch. We compliment each other," she continues. Keep an eye out for signs of flirting like a light touch on the arm, holding eye contact, or leaning in during the conversation. "If your BFF is sending any of this your way, there's a good chance they feel the same way," the dating expert explains.

Find a Playful Way to Broach the Subject

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Once you've decided that professing your feelings is the right move for you, it's time to find the perfect way to do so. Darcy suggests finding a lighthearted way to start the conversation like playing 20 questions. "Make sure one of the questions you ask is, 'Have you ever had feelings for a close friend?'" she explains. "If the answer is yes, you can ask increasingly more pointed questions like, 'What would your advice be to someone who had feelings for a close friend?'” It's a fun, flirty, and playful way to gauge their feelings as you prepare to reveal your own.

Be Direct

Transitioning from a best friendship to a romantic relationship is a minefield.

Healthy Relationship
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When making the transition from friends to dating, being open and honest is paramount. "Direct communication is the key to any relationship," according to Darcy, "but transitioning from a best friendship to a romantic relationship is a minefield." The best way to navigate this uncharted territory is to be direct from the start. That means clarifying what type of relationship you're going to have. Is this a friends with benefits situation or are you looking for a long-term relationship? Darcy explains that it's important to answer these questions from the beginning so you can both move forward mindfully.

Move On

Moving On
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As with most things worth fighting for, there's always the possibility of getting hurt. If your feelings aren't reciprocated, Darcy recommends using a bit of humor to address the situation and move forward. She suggests saying something along the lines of this: "As prepared as I thought I was for this possibility, I didn't work out a script for what to say at this point, so would you help me recover from this awkwardness?"

Once tensions are lightened, you can explain that you're committed to the friendship and that you're open to hearing how they feel about what you've told them. Clarify that you want to make sure the friendship isn't damaged, and then you can begin to move on.

Note that sometimes it won't be possible to salvage the friendship after an event like confessing your feelings, so be very sure that you want to do so before telling them. If you just want a quick fling, it may not be worth risking the friendship.

Read up on more love and dating advice from the experts below.

Jenna Birch The Love Gap $13
Ken Page Deeper Dating $12
Mandy Stadtmiller Unwifeable $12
Nichi Hodgson The Curious History of Dating $14
Sharon Salzberg Real Love $14
Amir Levine and Rachel Heller Attached $15
Ben Stuart Single, Dating, Engaged, Married $8
Ben Schwartz Things You Should Already Know About Dating, You F*cking Idiot $10
Guy Winch How to Fix a Broken Heart $12

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