How to Go From Friends to Dating

By | | Dating
How to Go From Friends to Dating
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It’s a storybook ending perpetuated by movies: A couple of best friends go through life as buddies, but all of a sudden they hook up, get married and live happily ever after. But does it happen in real life?

In short: yes, but if you want to know how to go from friends to dating, beware that it comes with certain risks. Think you’re up for the challenge? If so, here’s what you need to know.

Tips for making the friends to dating transition

If you’ve decided to try to turn a friendship into something more, know that you’re treading on territory where many have tried, with equal measures of success and, yes, failure. But to have the best chance, there are several questions to ask yourself, signs to look for and best practices to observe.

Determine why you think you want to date them

Almost everyone has had a thought cross their mind that they could go from friends to dating, but most people don’t pursue it––and for good reason. According to dating coach Connell Barrett, dating your friend puts you at risk of ending your friendship.

“It’s sort of like having all these chips at the blackjack table and saying, ‘You know what, I want to double down,’ and you risk losing all your money,” he said. “But at the same time you’re gambling on something that can be even more meaningful and incredible, which is a great, passionate, romantic relationship.”

Barrett recommends thinking about whether your feelings are a fleeting crush or if you think your friend is someone you could truly fall in love with.

“If you feel like there might be a spark, ask yourself: ‘Do I see long-term romantic potential or am I just having feelings because I care about this person?’”

Look for signs of mutual interest

Your next step in transitioning from friends to a relationship would be to assess whether your friend feels the same as you do about them, “because you really don’t want to even broach the topic unless you feel like there’s a reasonable chance that this person will either feel the same about you or be open to changing things from a friendship to a romantic relationship,” Barrett said.

Is your friend smiling at you and making eye contact? Are they touching you on the arm a lot? These could be signs they’re interested, but don’t jump to conclusions.

Broach the topic gently at first

You’re talking about a friend here, not a random Tinder date or stranger from the park––you owe them a clear explanation about your intentions. But do it gently.

“You don’t need to pour your heart out,” Barrett said. “You can just say to your friend: ‘Hey, you know what, I really enjoy our friendship, and I wanted to know if you were up to go out on an actual date to see if there might be more.”

According to Barrett, another example of what you could say is, “You know what, I’d love to go on a date with you. I feel like we have such a great vibe together as friends.”

The exact words aren’t important. What is important is that you communicate your feelings in a way that is clear and gives your friend an out if they want to stay just friends.

Don’t ask for too much

Surprising your friend by telling them that you want to have three babies together and move to the suburbs is probably not going to turn out too well. If you want to maintain the friendship even after you broach the subject of romance, start by asking them on a date or two. That way, if your friend hasn’t thought about whether or not they want to be romantic, the date could unlock those feelings.

“They want to see how they feel with you in a dating romantic context, as opposed to saying, ‘Hey let’s go from friends to a relationship,’ Barrett said. “That might be a bridge too far.”

Try some casual flirting

There’s a big difference between trying to make out with your friend and doing some casual flirting to see if you connect romantically. Be playful, offer them some genuine comments, smile, and show your interest by turning towards them when they’re talking. “A little bit more teasing and complimenting and pulling the proverbial pigtails,” said Barrett.

What you want to do is create “a romantic context” so you can communicate in a way that shows how you feel, rather than just telling them.

Be careful when intimacy gets involved

One thing led to another and now your friend is snoring next to you. What now? Well, things just got a lot more complicated.

Getting intimate with someone can change the way they see you and it might be difficult to go back to being just friends after hooking up. That’s why Barrett doesn’t suggest becoming “friends with benefits” if you hope things could develop into a long-term romantic relationship.

“Typically, one person is going to want something longer lasting because we’re wired to want that and that can create a problem if you’re in ‘friends with benefits’ zone and the other person’s in the ‘Wow, I’m really starting to feel something [zone],” he said.

What if we’ve been friends for years before dating?

There’s a big difference between a friend you know casually and a genuine, close friend. The strength of your relationship with a close friend is much stronger, but that also means it’s more fragile and vulnerable to betrayal. In addition to the above tips, keep in mind the following when trying to take a close friendship to the next level.

Being friends isn’t a bad thing

Congrats, you have a good friend! Those are hard to come by and this is certainly not anything to worry about if you want your relationship to evolve from friendship to romantic. In fact, it could be the start of something great.

“The fact that you are friends with this person is not a bad thing. It’s not that you’re in the friend zone necessarily,” Barrett said.

“In fact, it can be the basis of a great relationship because a really great relationship is based on, among other things, friendship, so that aspect is already there.”

Going from friends to dating simply adds the elements of romance and passion to something that’s already great, but it shouldn’t replace the friendship entirely.

Leave the romance for your alone time

If you and the friend are in the same social circle, your mutual friends will be talking about it––it’s inevitable. Keep the teasing and nosiness at bay for as long as you can by keeping any discussion of your feelings to yourself.

So don’t ask them out on a date when all your friends are listening or try to make your moves at a party. “It’s better to just be in your little bubble of potential romance, so that you can see how you feel about each other without worrying about what everybody else is thinking,” Barrett explained.

Awkwardness could be a bad sign

So you hooked up and, well, it was awkward. In that case, Barrett says it might be a sign you’re not meant to be a couple. However, some level of awkwardness could be okay.

“I’m not saying [there] should be zero awkwardness at first, we’re human, it’s okay to feel a little bit awkward,” he said. “But as long as you feel really passionate for each other and sexually attracted, then there shouldn’t be much awkwardness.”

You can possibly salvage the friendship

If after you expressed your feelings and maybe went on a date or two and it still didn’t work out, Barrett has some good news: going back to being plain old buddies is “definitely not impossible.”

As long as you tested the waters and went slow, you might be able to jump back in as buddies, but it’s not always a given. .

The pros and cons of going from friends to dating

As with any big decision, it’s wise to weigh the pros and cons before taking any action. While you may be able to talk yourself into a long list of pros (he knows me so well, she’s always seemed like she may be into me, we have the same sense of humor), the weight of some cons may be grave (she may never talk to me again).

Each situation is personal and the pros and cons will differ, but common ones include:

Pros:

A chance at a great relationship

Try as you might to snuff out those pesky romantic feelings for your friend, “the heart wants what it wants, as the saying goes,” Barrett said.

If your feelings are reciprocated by your friend, you could be on your way to having one of the best things there is––a loving relationship.

“There are a few things in life that are more satisfying, powerful and important as a great connected, passionate, relationship,” Barrett said.

You followed your heart

Even if things don’t work out romantically, you’ll have the knowledge that you followed your heart and living without regrets can feel pretty great.

Take it from a guy who used to have low confidence with women, but now helps teach men how to find love. “It feels good to be really authentic and go after what you want and to share how you feel with somebody,” Barrett said.

Cons:

Rejection

You knew before doing this that there was a chance at getting rejected. If your friend wasn’t into you in the same way from the start, or your romantic relationship fizzled out, it’s tough not to feel down about the whole thing. But you can’t take it personally.

“A powerful mindset is: ‘No matter what happens, they’re not rejecting me as a person. I know that this person cares about me because we’re friends. We have a deep emotional friendship connection,’” Barrett said.

“If it turns out that they’re not interested in me romantically, it’s not that I’m not enough, it’s not that I’m not attractive, it just means that I’m not their romantic type or mate.”

Losing the friendship

Sure, there’s a chance you could hook up and even go on a few dates, but there’s also a chance the relationship might not work out in the end––that’s the nature of dating, and relationships can end painfully. Sadly, if that happens there’s a good chance the friendship won’t make it either.

Conclusion

So, you have romantic feelings for your friend. The first step is to consider: Is it worth the risk of losing this friendship? If not, don’t risk it––a good friendship is hard to come by.

If you can’t resist following the butterflies in your stomach, look for signs that your friend might be interested. If so, ask them out on a date or two and if after flirting a bit you find there’s a spark, congrats, you successfully navigated how to move from friends to dating.

However, if things don’t work out, you have to take it in stride.

“It might just mean that this other person is The Beatles and you’re The [Rolling] Stones and that [you] just don’t go together that well,” Barrett said.

“But the Stones are awesome, it doesn’t mean you’re not awesome, it just means that you aren’t the right romantic fit together and that’s something you should not take personally and should not take as rejection.”

Disclaimer: The above is solely intended for informational purposes and in no way constitutes legal advice or specific recommendations.