Skip to main content

How to Start a Relationship With Your Best Friend

Andrea writes on various topics from dating, couples, astrology, weddings, interior design, and gardens. She studied film and writing.

Turning a Friend Into a Romantic Partner

Falling in love with your best friend is as simple as breathing air. People fall for their friends all the time! You grow with someone, you get to know their quirks, they suddenly become attractive in your eyes.

Who hasn’t had a crush on a friend? In some ways, the best person you could be dating right now is your friend that you’ve known for ages. You know what to expect, you don’t have to worry that they’re a total creeper, and you might feel more comfortable going on a date with them than someone you just met online.

You first want to make sure that your friend is getting the same vibes as you. Flirt a little and see what happens. Most people — who are really friends — are not going to totally freak out just because you seemed a little more into them. Do simple little things like open doors for them, move their hair behind their ear, get them little gifts, and text a little more. Throw some energy their way and see how they respond.

Confession Time

Make sure when you tell a friend that you like them that you’ve set things up just right. You want to be somewhere private and where they don’t feel put on the spot. Just in case things go poorly, you want to be somewhere that they can get away with ease.

Sometimes it’s a good idea to admit these things at the end of an event that way there is a natural progression toward saying goodbye or extending the night a little. Some people need a moment to process someone’s confession, so don’t be alarmed if they need a little space. If you’ve known each other for a while, it could be a big deal.

You want to make sure there are positive indicators before you make this jump. Does your friend seem interested in you? Are they reciprocating your advances? Are they suggesting a date themselves?

How to Date a Friend

1. Set up a convenient time where you can talk to this person one on one. Preferably during the day, on a weekday, or normal hours. Trying to convey feelings around the company of others is awkward and distracting. Plus, you want to give your undivided attention.

2. Don’t make a big deal out of it. Keep it short and sweet. Don’t lay on thick details about how beautiful their hands are and how much you want to hold them and how you think their lips are totally kissable. This might scare the living crap out of them, especially if they’re not interested in you. Tell them:

“Hey, I just want you to know that I think you’re really awesome. I would like to spend more time with you and get to know you more, and I think you might be interested in that too. . . and I’m sorry if I’m mistaken. I want you to know that I like you, and I’m curious how you feel about me.”

This is inviting, it isn’t aggressive, it lays out what you’re thinking clearly, it is concise, and it is open to conversation rather than manipulative. Do give them a moment. Say, “I know that this may be a lot to take in or you may not have ever considered this, so I can give you your space and know that if you’re not interested in me I still want to be your friend.”

They may not have considered you as a potential partner in your whole history. So yes, they may need a few minutes, a few days, or a week. Any longer than a week is cruel, and unless they generally are super indecisive, it probably is a “no” on their part.

3. Just because they are not interested does not mean you need to despair. In fact, I would say before leaving, especially if they do say no at that point say something like, “If you happen to change your mind at any point and I’m still single, feel free to broach this topic again.” People and their interests change so be open to that. They may not see you as a potential right now, but they may later.

Also, don’t become overly distressed and depressed. That isn’t going to help your case. You may feel that way, but don’t display it. Take some alone time to process your thoughts and feelings. Congratulate yourself for putting yourself out there — go buy a steak dinner. You didn’t do anything bad even if you feel bad. And now that your friend knows your thoughts. . . they may start to see you in a different light and that may take time.

Scroll to Continue

Read More From Pairedlife

4. They may be interested in someone else who they might 1.) succeed in getting into a relationship, or 2.) end up getting over. It may hurt when they get into a relationship, but play it cool. Over time, you will definitely find someone else. So don’t blow off your friendship just because they didn’t want to take it up a notch. Ultimatums don’t end well.

5. Whoever it is that you like, you can’t be certain that they will be available forever. You don’t want to treat them like a piece of meat you have to swipe directly from the butcher’s knife, but you do want to keep in mind that if they’re hot property then it’s guaranteed that someone else knows it too.

6. Before even getting to the point of confessing feelings, make them feel special. Figure out what they like and speak to their heart. You may win over or soften their heart. If you see them being less guarded and opening up, then you’re doing your job right. Friends usually start flirting more and changing their patterns when they’re ready to start dating.

7. If it’s your best friend… then you can trust them to handle this conversation. You don’t need to be pushy or over the top. Be yourself. Let them know it’s worth trying, the friendship won’t be ruined. You care about them, so you’re not going to throw everything away because feelings got in the way.

8. Keep your nosy friends out of it. When you start dating a friend, your whole friend group doesn’t need to know. In fact, your nosy friends could ruin things because they add too much pressure. Date in secret for a little bit, and if the romance builds let it unfold naturally.

9. Don’t turn things up from 0 to 100. Be patient with your new partner. You want to come off suave, charismatic, and romantic. If they like you back, don’t intensify things too quickly. That could make your friend run. Slowly add in more affection from dates, flowers, holding hands, and a kiss on the cheek. If they reciprocate, they’ll give back the same energy.

10. Rejected? Play it cool for a while. Don’t spam their phone and email with messages. Let things simmer down for the next couple of weeks. Invite them to something chill in the future, like grabbing pizza and playing video games. Keep it casual, and show you’re still friends. The awkwardness will die down after a period.

11. Don’t move on to other friends from the same group. Some people will ask one person out, they’ll get a no, so they’ll go down the line asking people from that same friend group if they want to date. The more times you do this the worse you’re going to look. People talk, so they’ll know you’ve already asked out Nancy, Katie, Hannah, Monica, Sarah, and the likes. This looks bad, desperate even. Now, if something naturally comes up, go for it. But asking lots of people from the same friend group for dates and not getting anywhere is a bad strategy.

12. Do not suddenly turn mean and cold. If you think you’re going to turn into a total jerk if you get rejected then you’re not emotionally mature enough to be testing these waters. You’ll come off less attractive than you started if you get rude when your friend gives you a no.

Act cool, calm, and collected. You’ll impress the person more. You want them to be impressed with you. If you seem mature, you may one day find yourself at this crossroads again, and the second time around things might go more in your favor.

13. Dress for the part. Look nice, smell clean (not overwhelming), and brush your teeth. When you like someone you should start dressing nicer. It will help them to see you as a potential suitor. Get the nice haircut, wear the shiny shoes, and lotion up those hands.

14. Don’t languish forever if they say yes. Get excited, but don’t go on about it forever. Ask them if they would like to go on a date, get dinner, go to a museum, something special. Try to move things forward, but please, don’t make too big of a deal. Avoid awkwardness.

15. Can’t speak your feelings? Write a message or letter. I think the bulk of the way people have confessed their feelings to me were through writing. It’s convenient, it’s quick, and it gives the other person the space to think. This should be done after you’ve gotten some indications that the other person might be interested.

16. Keep things natural and smooth. If you feel like you’re having to force yourself to do a confession, you’re doing it wrong. Telling someone you like them should feel natural, and it often happens quickly and succinctly. It doesn't feel like a major interjection.

© 2013 Andrea Lawrence

Related Articles