First, know that it’s totally normal to fall for a friend: Studies indicate that most of us find people more attractive after we get to know them (which might explain why so many of us feel like we never meet anyone we actually like on dating apps). But asking a friend out can be a lot more intimidating than messaging that Tinder match.
“Dating a friend comes with risks, such as the possibility of breaking up and losing a good friend, or even your social group falling apart if both parties hang out with the same friends,” says Maria Sullivan, dating expert and VP of Dating.com. “However, dating a friend can also lead to true love, so it is always a good idea to give it a try if you believe it will lead to something great.”
Keep in mind that even if the romantic relationship doesn't work out, the friendship doesn't have to end. "Just because a relationship didn’t work out doesn’t mean the ex-couple can’t try and go back to the way things were before they started dating," Sullivan points out. "Hanging out with mutual friends in a group setting will help to maintain a friendship, and as time goes on it will begin to go back to normal.”
We talked to people who have dated friends to find out their advice.
LARPing Friends
Jameson Hampton, 29, Buffalo, NY
The friendship: Jameson originally met their partner Isaiah playing a live-action role playing game (LARP) in 2008. ”For the first year or so of our friendship, I only knew him by his character’s name!” Jameson says. As time went on, Jameson and Isaiah began hanging out outside the game, along with other friends. After Jameson left the LARP group, they and Isaiah fell out of touch for a time, but later reconnected.
The relationship: In 2013, “I started getting these wild, cryptic texts from an unknown number, talking about weird rituals, and eventually asking me to meet at midnight in the local dog park (it was a reference to Welcome to Night Vale, which I was really into),” Jameson says. “My best friend and I showed up, not knowing for sure if it was a prank or what, and he was there and he’d roped a few friends into wearing cloaks and holding crystal balls. We drank wine in the park in the snow all night.” Now, Jameson and Isaiah consider that night their first date: “We were just kind of together after that.”
Jameson came out as transgender in 2014, after they and Isaiah had been dating for a year. Isaiah “was my biggest supporter,” Jameson says. They got engaged in 2016 and were married in September 2019.
The advice: “I think dating friends is great,” Jameson says. “Any good relationship should be built on a solid friendship. I get that people worry about ruining their friendships, but honestly, I think a really solid friendship should be able to survive trying to date and then deciding not to.”
High School Friends
Charlotte*, 28
The friendship: After meeting at a summer job, Charlotte* and Dan* (not their real names) were friends throughout high school and into college. “He'd come over my house all the time and knew my family really well. Basically the perfect high school guy friend,” Charlotte says.
The relationship: Charlotte had always had a crush of Dan, but during her freshman year, she began to realize that he might like her, too. “I kissed him one night when we were hanging out, and that turned into us casually dating,” she says. A month later, they made it official. “We really liked each other, but things started to break down as they do, and it definitely didn't help we were long distance the entire time we were dating,” Charlotte says. “We dated for two years and then had a horrendous break up (he dumped me over the phone!)”
It took a couple years, but they became friends again. “After I got over the anger and hurt, I was able to remember that he's awesome and all the reasons why we were friends in the first place,” Charlotte says. “It's honestly been one of the victories of my adult life to regain this friendship as purely that, a friendship.”
The advice: Charlotte advises people considering asking a friend out to “really think it through. Will you be devastated if they say no or it doesn't work out? Will you be okay if you guys break up and can't be friends for a bit? If you've seen them in relationships, how do they treat the people they're with?”
Comedy Class Friends
The friendship: Years after she and Dan broke up, Charlotte became friends with Will* after they took a comedy class together. They’d go to each other’s shows and text each other when they felt anxious at parties. After Charlotte ended a long-term relationship, Will began to hang out with her “more persistently.” “At first I didn't think much of it, and then I kind of slowly realized he was trying to ask me on dates,” she says. She decided to “roll with it” and developed feelings for him, too. After Charlotte threw a party, Will stayed to help clean up. “We ended up hooking up and dating for a while after that,” Charlotte says.
The relationship: Unfortunately, Will “was a total jerk while we were dating,” Charlotte says. “While it started out great and he seemed really serious about me, about a month in, he started to pull away and kind of restructure it as a friends-with-benefits situation.” Will was rude over text, would cancel plans often, and eventually dumped her over text. “It hurt because we started out as friends who were kind and reasonable with each other, but once we were dating, he started treating me like garbage,” she says. “I haven’t seen or talked to him since, which is okay with me. I have no interest in being friends with him anymore.”
The advice: “Relationships are a leap of faith for everyone, but when it's a friend, I think you have to be especially mindful,” Charlotte says. “If you think you'd be lost without the friendship, I'd advise against it.”
Better Off Friends
Ellie B., 22, New York, NY
The friendship: In high school, Ellie became friends with a boy in her English class. They began hanging out one-on-one which “gradually escalated into dating. Or at least kinda-dating.”
The relationship: "We were having sex, going to the movies, yet explicitly calling each other 'boyfriend' and 'girlfriend' took a lot longer," Ellie says. They did eventually each other “boyfriend” and “girlfriend,” but still, “it was clear that both of us wanted different things and neither of us was emotionally ready for what the other person wanted,” Ellie says. "I wanted the mushy romantic. He felt the opposite way.”
Ellie's then-boyfriend didn’t take her out with his friends often, and she felt like “this very secretive thing separate from the other people in his life.” Eventually, he broke up with her. For the rest of high school, they didn’t talk much, but then over the summer, they reconnected. "We resumed our friendship, continued having sex periodically, but never thought about progressing our friendship beyond that," Ellie explains. Now, Ellie is in a serious relationship and is "close friends and confidants" with her ex. “Despite our attempts at romance, ultimately our friendship proved more secure, and something we both valued more than the demands a relationship brings.”
The advice: “When preparing to ask out a friend, it’s important to accept that there’s always a possibility that you may lose the friendship if the relationship goes sour — either temporarily, for a few weeks, months, even years, or you might not reconnect all,” Ellie says. “You should remain conscious of the fact that no matter how secure your friendship dynamic is now, it will change in some way.”
Post-Breakup Friends
Rhys, 24
The friendship: Rhys and their girlfriend were friends for a year and a half before dating. They played Dungeons & Dragons and would watch movies together, but weren’t super close. “The way we started dating was kind of a mess,” Rhys says. Their now-girlfriend was dating Rhys’ close friend, who was falling for Rhys’ best friend. “It quickly became a weird love triangle,” Rhys said. Rhys had recently broken up with their boyfriend, so Rhys began consoling their now-girlfriend to help take their mind off their own breakup. The two began spending more time together one-on-one, mostly watching TV or playing video games.
The relationship: As Rhys and their now-girlfriend were hanging out, she began casually saying, "I love you." Rhys would usually respond, "Me too," but one day, they said, "I love you, too." The way their now-girlfriend reacted made Rhys "connect the dots." They add, "It was awkward because I hadn’t really thought about another relationship. I’d only recently discovered I was a lesbian, and the friend group was really fragile, and my situation at home was tough. But she made everything so much better and easier.” They began dating, and now, they’re still together and planning on getting married in two years. “Even though my home life is touch and go, I always know that everything gets softer when I hear her voice. I know that she'll always be there for me," Rhys says.
The advice: “I know people worry about losing a friend, but that sort of thing almost never happens in real life,” Rhys says. “Even if your friend turns you down, be open and honest and expect the same in return.”
College Friends
Samantha, 23
The friendship: Samantha and her ex met in college and were friends for over two and a half years before dating. "Eventually we were best friends, talked every day, and we'd even give each other advice on dating other people," she says. "I’d help wing woman him with girls he was into or listen to him cry about his ex-girlfriend." Samantha was in a relationship when they first met, and she wasn't initially into her friend. "I don’t think there were instant feelings on either side at the beginning until we both got a bit older and glowed up," she says.
The relationship: During their junior year of college, both Samantha and her soon-to-be boyfriend were single and into each other. "It took friends pushing us together at a party to get us to stop being cowards and confront our feelings," she says. "We had both been going with different dates to a college party and our dates conspired to get us together instead. Eventually all the hinting became obvious, so my soon-to-be boyfriend pulled me aside finally and asked if I had feelings for him. I said yes, and boom, suddenly we’re making out." They planned an official first date and became boyfriend and girlfriend shortly after.
But then, the ex broke up with Samantha after eight months of dating. "We did not talk for a while after. I was very heartbroken and he started dating someone new," Samantha says. After the new girlfriend dumped him, he and Samantha rekindled their friendship, and eventually became friends with benefits. "Messy, I know," she says. "After the second time we 'got back together,' it ended a few months after the end of college, and we no longer speak. He changed a lot over the four years I knew him."
The advice: "It could be amazing, but like all relationships, if it ends, it’s not likely it’ll be on good terms," Samantha says. "And don’t let your potential partner convince you that it won’t end badly! A lot does change when you add sex and love to a deep friendship."
Finally More Than Friends
Camille
The friendship: Camille met her now-fiancée, Merle, during her first year of college. They quickly became close. “We spent a lot of time together, and it was the best friendship of my life,” Camille says. “I even got excited for her when she got a hot boyfriend.” As time went by, “I began feeling on edge around her without knowing why,” Camille says. Because she hadn't fallen for Merle the day they met, she didn’t understand that she had slowly developed romantic feelings. “Then it hit me in the head and, after many misunderstandings, we began dating,” she says. Merle was the one who made the first move, kissing her while drunk after many hints from Camille. “All our friends said, ‘At last!’”
The relationship: After ten years of friendship and seven years of dating, Camille and Merle are now planning their wedding. “She is the best thing that happened to me,” Camille says. “I have never been afraid to be myself around her because she already knew me, and it is the best feeling. I feel so safe and loved.”
The advice: “Dating a friend is amazing, 10/10, would recommend.”
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