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Dating A Friend You’ve Known For Years Can Be The Best (& Most Terrifying Thing) Ever

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Relationships are complicated in and of themselves, but when it comes to turning a friendship into a romance, the transition can be especially tricky. With your feelings, and of course, a friendship at stake, dating a friend you've known for years can be the best — and most terrifying — thing ever.

Needless to say, the deciding factor is whether or not your feelings are returned, and whether you gain a significant other or lose a close confidant. But while the future may be uncertain, experts say that there is a way to cross the line cautiously so as not to catch your crush off-guard and, at the very least, preserve your friendship if the attraction isn't mutual.

Ahead, you'll hear from therapists who dish on the challenges and triumphs that can come with dating a friend, as well as one woman who tried it, herself (spoiler: It didn't work out in the long run). The gurus also give their pro advice on how to decide whether to pursue a romance and the best ways to go about it.

If you've been thinking about sharing your "more-than-friends" feelings with someone you care about, read on to determine whether it's worth the risk.

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Weigh The Pros & Cons / Prepare For All Possible Outcomes

Before blurting out "I love you" to one of your buds, it's important to think everything through. "In a situation like this, you have to be prepared for all possible outcomes," says Dr. Valeria Chuba, integrative sexologist and host of the Get Sex-Smart Podcast. "It may sound a bit cold, but with so much at stake, running a cost/benefit analysis on your potential romantic involvement with a friend before you confess your feelings can be really helpful."

She continues, "If you do decide to go ahead and pursue romance with a friend, it's very important to not get too attached to a positive outcome. You may get lucky and find out that your friend reciprocates your romantic feelings; but it's just as likely that he or she isn't interested in anything beyond friendship."

Signs They May Be Interested, Too

Of course, it's helpful if you have an inclination whether your friend has feelings for you, too. But Dr. Sue Varma, a board-certified psychiatrist and couples and sex therapist on faculty at NYU Langone (@doctorsuevarma on social media), warns that some signs are up for interpretation. "When we perceive mutual attraction — the key word being 'perceive' — it is tempting to pursue and make a move such as trying to kiss the person," she says. However, she advises against the Hollywood gesture. "If there is a long-standing friendship, it is worth being sure that you are accurately perceiving [the attraction]."

She shares some possible signs of a mutual crush:

  • "The person is seeking more opportunities to spend time with you and it’s happening even outside of a group."
  • "They are sharing more intimate details and personal information."
  • "They want you to meet their family."
  • "They start to get jealous or possessive when others want your attention."
  • "They are flirting with you; making comments about your physical appearance, attractiveness etc."
  • "Their body language, like touching, eye contact, and opportunities to be physically close are increasing."

Be Sure To Take The Pressure Off

Remember that spilling your feelings may catch your crush off guard, so be careful to keep it light if you do. "It's on you to make it clear to your friend that regardless of whether or not they are interested in you romantically, your friendship will always come first and you won't take their lack of romantic attraction personally," reminds Dr. Chuba. "Tell your friend that you are simply sharing what is in your heart on the off chance that he or she shares your feelings, without any expectation of reciprocity."

Further, she says, they deserve some space to think things over. "Give them as much time and space as they need to respond. And if they have no interest in pursuing romance, be gracious and respectful of their 'no,' and don't hold it against them."

How To Handle Getting Turned Down

They say to hope for the best and prepare for the worst, and should your feelings go unreturned, it may be helpful to have a little speech planned to help preserve your current friendship. "You can say, 'I love our friendship, and thanks for being open with me. I respect that [you don't feel the same way] and I’d still love to be friends and hang out if you are okay with that.'"

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Potential Pitfalls

There are challenges in any relationship, but friends-first couples may experience some additional hurdles. Michelle* became good friends with a man named Sean, and after three years, "I had the random realization that sometimes the best guy for you is the guy you've friend-zoned," she says. "I entertained the idea of Sean and I becoming a 'thing,' and told him I had feelings for him and wanted to see where it goes."

It turned out that their feelings were mutual, and they went on to date for five years. But eventually (and despite their close friendship), she realized that the key ingredient that bridges the gap between platonic and romantic affection — attraction — was missing. "Sean and I had an amazing friendship and had been through so much together," she shares. "Not a single person knew me the way he knew me. But I never felt I desired him the way he did me. I wanted to be in love with him, but eventually came to terms with that the fact that I wasn't and could never be. I realized that it wasn't fair to him or me, so I ended things."

While breakups are never easy, a split with someone who started as a friend can feel like a double loss, especially if they're more emotionally invested. "I admitted to him that I wasn’t in love with him; his heart shattered right in front of me," she recalls. "It was one of the most difficult things I ever had to say to someone."

For the record, it is possible to be friends with an ex. But if you were buds to begin with, it may never be the same, or you may even lose that companionship entirely. "We have tried to maintain a friendship and succeeded at some points," says Michelle of her former beau. "But he is still in love with me and believes we will wind up back together."

Now, she's dating someone new. "Part of me wishes I didn't keep [Sean] in my life after the break up because I wouldn't have to share this painful reality [of a new relationship] with him. But the other part of me would never wants to lose the most valuable friendship I've ever had."

Unpacking The Best-Case Scenario

Onto the positives: If your pal-turned-partner works out for the long-haul, you could enjoy a relationship that's long-lasting and fulfilling. After all, don't happy couples say their significant others are also their best friends?

"Transitioning from friendship into romance can be absolutely wonderful and can have great benefits," Dr. Chuba points out. "Being friends means you genuinely like each other, you have seen each other at your best and worst, and you trust each other. This is a really strong foundation for a romantic relationship. At the same time, be prepared to learn new things about each other and see each other in a completely new light. You already know each other as friends; now it's time to get to know each other as lovers."

*Name has been changed for anonymity.