How to Go From Just Friends to Dating, According to an Expert

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It's no secret that falling in love is easy. In fact, some argue it's the simplest part of a relationship. Commitment, compatibility, and trust are what tend to be more difficult to manage, especially if the person 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," says relationship expert Dr. Darcy Sterling, a therapist and the former dating and relationship trends expert at Tinder.

Meet the Expert

Dr. Darcy Sterling is a licensed clinical social worker and the host of E! Network’s hit show Famously Single. She and her wife, Stephanie Sterling, own the New York City-based therapy practice Alternatives Counseling.

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.

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

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

Ask Yourself the Real Questions

Think long and hard about the decision to put yourself out there (something you've likely already spent a good amount of time doing). To help make your daydreams a bit more productive, Dr. Darcy poses a few enlightening questions to determine if the risk is worth the reward (or potential heartbreak).

First, there are the basic, logistical questions to consider: Are you both single? Are you both looking for the same kind of relationship? According to Dr. Sterling, if the answer to either of these questions is "no," it's probably not worth the risk. "Relationships are hard enough to maintain when people are compatible," she points out. You're likely going to harm the friendship you already have by attempting to change the game under these circumstances.

Relationships are hard enough to maintain when people are compatible.

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

Look for Signs of Flirting

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," Dr. Sterling 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

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. Dr. Sterling 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 Open and Direct

When making the transition from friends to dating, being open and honest is paramount. "Direct communication is the key to any relationship," according to Dr. Sterling, "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? It's important to answer these questions from the beginning so you can both move forward mindfully.

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

Respond Gracefully to Unreciprocated Feelings

As with most things worth fighting for, there's always the possibility of getting hurt. Dr. Sterling recommends using a bit of humor to address the situation and move forward if your feelings aren't reciprocated. 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?"

It won't always be possible to salvage the friendship after confessing your feelings, so be very sure about your decision to do so. If you just want a quick fling, it may not be worth it.

Once tensions lighten, you can explain that you're committed to the friendship and 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.

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