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A man giving a red rose to a smiling woman.A man giving a red rose to a smiling woman.

How to Ask Someone Out After a Long Friendship

By: BeSeen Team

Date: June 14, 2023

So, there’s someone special in your circle, and you want to take your relationship from platonic to romantic. But you’re a little rusty, or you’ve never been in a position where you wanted to date a long-time friend. Maybe you’re just plain nervous and don’t know how to get the ball rolling. Whatever your hangups, here’s how to ask someone out without totally jeopardising your friendship. 

Is It Okay to Ask a Friend Out? 

Asking a friend out is a big decision, so it’s normal to be on the fence about it. Should you try to kill your feelings until they fizzle out and fade away? Or should you act upon them? In any case, make sure you carefully think your decision through.

Dating expert Maria Sullivan shares her two cents with lifestyle magazine Refinery: “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. 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.” 

How to Ask Someone Out When You’re Friends 

A man deep in thought in front of a window.
Take time to reflect on your feelings before you make any major moves.

Ready to explore a new phase in your friendship? Make it happen with these steps! 

Step 1: Assess your feelings. 

Before you make your big move, you’ve got to figure out your feelings. Do you think this might be a simple case of infatuation? Maybe you just got out of a relationship, and now, you’re looking for another outlet for your affection. Are you in a vulnerable place and craving comfort from someone you trust?  

If any of these ring true for you, you may want to hold off on asking your friend out. Sometimes, fleeting fancies can disguise themselves as something deeper than they are. Throwing all caution to the wind based on an unstable foundation can complicate your friendship. It may not be worth it in the long run. 

On the flip side, maybe you’ve realised that this person is the best part of your every day. Do you feel at ease with them in a way that you don’t with anyone else? Perhaps they’ve given you signals that they like you, too. You’ve come to believe you share the same values – and that you’ll make a good team. 

These could be signs that you’ve stumbled upon something rare and worth pursuing. There are still risks, but now you’re putting yourself out there for a once-in-a-lifetime type of connection – at least, potentially. No matter how it goes, these are the kinds of feelings you should take a chance on. 

Step 2: Get the timing right. 

Have you ever heard the phrase, “timing is everything”? Making your move at the right time could bring you closer to your desired outcome and farther away from a not-so-ideal one.  

Before you lay your feelings bare, ask yourself if your friend is in the best place to receive them. You might be ready to transition your friendship into romance, but you have to consider the spot they’re in, too.

Not sure how to ask out a good friend without making them feel awkward or ruining your friendship? You’ll never be 100% certain how they’ll react until you finally ask them. Still, you can set yourself up for success by checking in with them first to get a better read on the situation. 

Step 3: Make it a private conversation. 

A man and a woman chatting in a coffee shop over drinks.
Find a quiet, private place to chat, just the two of you.

No one wants to be put on the spot and pressured into responding favourably because other people are watching. Since this is a private matter, keep the conversation between yourselves. 

If you want to know how to ask out your best friend face-to-face, catch them when they’re alone and somewhere comfortable. Are you a planner? Schedule solo time with them at your favourite café but keep it casual. As serious as you may be about dating, try to keep the discussion light. Say your piece, then give them space to think their answer through. 

Does an in-person chat seem like too much? Don’t worry! You have other options: 

  • Shoot them a message if that’s more your speed. It’ll also let you breathe between exchanges, so nervousness doesn’t get the better of you. 
  • Ring them when you know they’re not busy if you want something more personal than a DM. 
  • A video call is the perfect middle between doing it in person and over the phone. You get to gauge their reaction, but you’re both free to jump off if it gets awkward. 

Step 4: Be cool, calm, and confident. 

A man and woman having coffee together while the man smiles brightly.
Be confident and show them what they’re missing out on.

Play it cool and lean into your friendly rapport but make it clear that you’re serious about asking them out. Confidence is key here. Go into that conversation with your head held high. Show them you’re secure in yourself and ready to bring that energy into your dates should they say yes.

But make sure it’s not all for show. If you struggle with confidence, keep working on it. Think about what’s at the root of your insecurities and invest in the appropriate self-care methods to address them.

For example: do you have crooked teeth that make you want to hide your smile? Time to consult your dentist! They may recommend ClearCorrect aligners to target misalignment. Unlike traditional braces, these devices are nearly invisible, so no one will know you’re wearing them – not even your date! They’re comfortable yet effective, applying gentle and consistent force to straighten your teeth.

Of course, you shouldn’t jump into orthodontic work and other long-term treatments for someone else. It’s a commitment (just like a relationship!), so you’ll want to do it for your benefit. At the end of the day, prioritising yourself will always be the best thing for your self-esteem. 

Step 5: Wear your heart on your sleeve and respect their decision. 

Now that you have their attention, it’s time to be brave. Tell them how you feel and why you want to try for a romantic relationship. Leave your pride at the door, ignore the urge to play mind games, and let yourself be vulnerable. If you’re good friends with this person, you should be able to trust them with your honest feelings.  

Likewise, be prepared to accept their decision, no matter what it is. They might tell you they’re not ready yet, but they’ll take you up on the offer later. Perhaps they’ve been waiting for you to make a move and they can’t say “yes” fast enough. Or maybe they only see you as a friend – it’s a bummer, but quality friendships are never a consolation prize. Remember: even if romance is off the table, your platonic relationship is still worth cherishing. At least you tried! 

Now that you know how to ask someone out, you’re ready to shoot your shot. Power through the nerves, keep your chin up, and flash them a big, bright smile. Deep breaths – you’ve got this! 

 

Reference: 

Smith, E. W. (2023, December 11). The Pros & Cons Of Dating A Friend — From People Who’ve Been There. Refinery29. 

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