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What To Know Before Dating A Friend – Our Checklist

Kathleen CramptonKathleen Crampton
Kathleen Crampton
6 min read
Published in Compatibility 


    Considering a romantic fling or partnership with your best pal? Here’s everything you need to know before going on a date with a friend.

    Going on a date with a friend can be an exciting risk, but it may also come with the pressure to do it right. If you’re considering a romantic fling or partnership with your best pal, there are some things to keep in mind before diving into the muddy waters of a friendship-turned-relationship:

    • Interpret the signs correctly
    • Have the “define-the-relationship” talk early on
    • You already share common ground
    • You know their best (and worst) qualities 
    • The transition from dating to relationship might be awkward
    • Your friend group dynamic might be affected
    • How they treated past relationships might be how they treat yours
    • Your friendship bond can be a solid foundation
    • Ask yourself if it’s a risk worth taking

    Here is our complete list of what to know before dating a friend.

    1. Make sure you’re reading signs correctly.

    There’s nothing worse than misinterpreting a smile or a flirtatious quip as “I want you” and then realizing that you’re alone in your feelings. A good friendship might include natural flirting now and then, especially with the more time you spend together. But that doesn’t necessarily mean either of you sees the other as relationship material or someone worth pursuing past friendship. 

    Don’t let your crush blind you into reading into every remark, look, or touch. It can be difficult to like someone as more than a friend and not know if your feelings are reciprocated, but try to take it slowly and wait until you have sufficient signs that they might be into you. 

    1. Define the relationship ASAP.

    While you can interpret flirtation as much as you want, your own internal thoughts and feelings only go so far. That’s why it’s super important to get on the same page as quickly as possible. This could mean making the first move or simply sitting down and telling your friend how you feel. If they share your feelings, then discuss what this new reality looks like moving forward, if you should give dating a go, or if it’s better to leave your platonic friendship untouched. 

    If you want to know how to date a friend, the name of the game at the beginning is vulnerability. It takes guts to expose your true feelings for someone, but it’s often the best way to know exactly how they feel (no more guessing!) and get on the same wavelength. 

    1. You already share common ground.

    Chances are that you have things in common with this person. Heck, your friends for a reason, right? Dating a friend brings with it a sense of comfort knowing that you already share similar interests, passions, and hobbies. Maybe you originally connected over trivia at your neighborhood pub, through a local running group, or at a dinner party hosted by a mutual friend. However your friendship spark ignited, “shared interests” is one more thing to check off of your future-someone list. Plus, you can skip the getting-to-know-you small talk at the beginning. But if you’re ever in doubt, check out our helpful tips for a first date with a friend.

    1. You know their best (and worst) qualities.

    Friends have a front-row seat to the “who-you-really-are” show. When you spend time together, you can see how they treat people, how they respond in certain situations, how they talk about their family and friends, and so on. 

    Because you’re friends, you already know this person’s best qualities and the traits you could do without. That’s a huge step up from meeting someone for the first time. But it can also come with the weight of having to make a big decision: whether these qualities fit your ideal mate. When you’re seeing people you just met, it might be easier to let them go when something is revealed that you don’t like. But when it’s your friend-crush, you might feel more indecisive because you already have a shared bond.

    1. The friends-to-dating transition may be awkward.

    Don’t expect the relationship switch to turn on automatically once you both decide to pursue romance. Things like PDA, physical intimacy, and knowing how to act around your group of friends might be a little awkward at first. And that’s ok! Dating a long-time friend might feel strange at first. Give yourselves grace in the process and keep humor at the forefront. Laugh when a first kiss is weird or your friends tease you. They’re just tiny relationship speed bumps that you need to cross.

    1. Keep your friend group in mind.

    If you’re both part of the same friend group, try not to involve the others in your relationship at first. While your relationship is about the two of you and you shouldn’t worry about what others think, it might take your other friends time to adjust to the idea of you both being together. Make sure the decision to date doesn’t incorporate the opinions of everyone else. 

    It’s also a good idea to remember that the friend group dynamics might change if you both break up. If things don’t work out, some friends might side with you and some with the other person. While it’s helpful to remain hopeful that things will go back to normal if your date with a friend goes south, don’t let your rose-colored glasses keep you from preparing for reality.

    1. How they treated past relationships might be how they’ll treat yours.

    Take note of how your friend treated past relationships. Were they kind? Did they treat their significant other with respect? Did they show love and put in the relationship work? How did they talk about their S.O. to you and your friends? When the relationship ended, did they blame everything on the other person?

    The answers to these questions will help you decide if being in a relationship will be a good experience or if you should save yourself from future heartbreak and stay just friends. This isn’t to say that people can’t change their behaviors, but you can get a good feel for how you’ll be treated by assessing how your friend treated exes. 

    1. Your bond can lead to a strong relationship foundation.

    If you’ve ever asked a couple who’s been together for years what their secret is, there’s a good chance that they said, “Make sure they’re your best friend.” While there are definitely other equally important factors (respect, love, kindness–you get the idea), if you’re dating a long-time friend, all of these are probably already present in your relationship. You’ve set the foundation of mutual respect from the get-go, which can pave the way for a meaningful relationship–no matter how long you date.

    1. Ask yourself if it’s a risk worth taking.

    You’re probably wondering if dating a friend can ruin a friendship–but only you know what’s at stake. Is the potential of losing them as a friend if you break up worth the risk of pursuing a meaningful relationship right now? 

    Consider making a good ol’ pros and cons list. Write down every benefit and every downside of starting a relationship together. This may provide clarity when there are so many emotions, thoughts, or worries swirling around in your head. And if that doesn’t give you peace either way, seek the counsel of people you trust, whether that’s your parent, a mentor, or another friend. They might have experience with this exact situation and can give you sound advice. 

    Good friendships can become good relationships–you just need to know how to handle the initial conversations, interactions, and transition and understand what questions to ask yourself before you dive in. A date with a friend doesn’t have to be a loaded situation, but it’s important to understand the nuances and potential risks of letting that date evolve into a relationship. Sometimes, it’s a risk worth taking.

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