10 Useful Tips For Dating Your Best Friend

Dating your best friend

Mila Kunis and Ashton Kutcher, Blake Lively and Ryan Reynolds, Sheryl Sandberg and Dave Goldberg, what’s common between them? All these couples were best friends before they dated and got married. Transitioning from the friend zone to the relationship zone is exhilarating but it could prove to be difficult at times. Dating your best friend, as fairytale-esque as it might sound, can turn into a giant nightmare if you aren’t careful.

If your best friend is in love with you and you too feel the same way about them, then there’s no doubt you are ready for starting a relationship with your best friend. Before reciprocating their feelings, there are certain factors that should certainly be taken into consideration.

So, what exactly do you need to keep in mind before you get into a relationship with your best friend? Is it worth it? Will it ruin things? What are the pros and cons? Let’s answer all your burning questions so you can take your dynamic with your bestie to the next level.

Starting A Relationship With Your Best Friend

According to a study shared by CNN, 83% of adults in relationships considered their partner to be their best friend, and 44% of college students indicated that their best friend was also their romantic partner. These statistics do suggest that being in a relationship with your best friend is not uncommon. However, to make your relationship last, there are certain rules of friends to dating transition that you should be mindful of.

When you start dating your best friend, the dynamics of your friendship change. They are still your best friend, but you will now be romancing this person and that is kind of scary. The proposition of getting romantic with your best friend can leave you both feeling like you’re grasping at straws to stay afloat.

The initial days of dating your childhood friend or best friend are a bit confusing and awkward. You want to hold hands, hug and kiss, but feel shy and awkward like high school kids thinking whether it’s too early or inappropriate. The idea of holding hands with a person who you once treated as a sibling in your childhood feels weird in itself.

All kinds of thoughts come into your mind once you’re in a relationship with your best friend. You might be worried about whether this is a bad idea since it could hamper your friendship and change literally everything. Dating your best friend can feel like a whirlwind of emotions. However, once you smoothly sail through the different friends to lovers stages and find a comfort level as romantic partners, it can prove to be the most beautiful relationship of your life.

You already know each other like the back of your hand and share an unparalleled comfort level. Now with love and romance thrown into the mix, you can build the most wholesome relationship possible. If you’re struggling to figure out just what you need to do, here are 10 useful tips for dating your best friend.

Related Reading: 10 Signs You Are Moving From Friends to Lovers

10 Useful Tips For Dating Your Best Friend

Falling in love with your best guy friend or girl friend can be a little unnerving. You may spend a lot of time confused about your feelings. Once you accept your changing feelings toward them, comes the part where you endlessly wonder if your best friend is in love with you too.

Did they just agree to this because you two get along so well? Is s/he only in it because they’re settling? Needless to say, getting used to being in a relationship with your best friend isn’t the most straightforward journey.

Best friends to dating transition can truly be a long-winding process. It’s only natural for you to want to tread carefully. After all, you don’t want to lose your most special friend to a hasty decision. When all the due deliberations are over and you finally decide that you want to take things forward, you’d want it to last. For that, here are 10 useful tips for dating your best friend that will hold you in good stead:

1. Don’t rush things

You are still figuring out your feelings and your way around the relationship at the start of the relationship. You’ve said yes, but you need to accustom yourself to the “boy” or “girl” factor replacing the “best” before the “friend”.

The first step is to establish an emotional connection between you both, which you never shared when you were best friends. This will make the foundation of your relationship strong and help in the transition. Thus, it is important to build a connection as only feelings and chemistry aren’t enough to keep the relationship going.

If you want it to stick, you need to be patient and understand each other at an emotional level. Falling in love too fast is never a good idea. Try to take your relationship forward one step at a time rather than making giant strides from the beginning.

For instance, sleeping with your best friend soon after you’ve both admitted your feelings for one another may not be the best idea. Or eloping and getting married on an impulse just because you’ve been friends for years before dating can backfire.

2. Manage your expectations

When you are dating your best girl friend or guy friend, you expect more from them than from a regular relationship. You expect them to know you from inside out and thus not hurt you. You need to understand that nobody is perfect, not even your best friend.

Even your best friend, now boyfriend or girlfriend, is bound to make mistakes and there will be times when all will not be roses. Fights, hurting, misunderstandings and lots of drama come as a part of the package in every relationship, even one with your best friend.

It’s easy to let your expectations run wild when you’re dating a best friend. They should know every single thing about you by now, it’s only natural to expect them to magically calm you down when you’re angry or cheer you up when you’re sad, right?

You need to treat this relationship like a normal one and manage your expectations accordingly. After all, they’re human too. Even though you may have been friends for years before dating, new facets of their personality will emerge once you’re in a relationship.

3. Be honest

falling in love with your best guy friend
You don’t need to pretend or hide your true feelings from your best friend now that you’re dating them

The best thing about falling in love with your best guy friend or being in a relationship with your best girl friend is that you can be open about your feelings. This person knows the real you and you don’t need to hide your true self from them.

Unlike any other relationship, where both partners spend the honeymoon phase putting their best foot forward and being at their best behavior when starting a relationship with your best friend, you can just be yourself. They probably know more about you than any other person on this earth does.

Be honest about your feelings with your partner. No matter how bad it is, you will always get a hug from the other end. This is one of the perks of dating your best friend.

Related Reading: 11 Dating Tips For Beginners

4. Know the stakes

Always remember the fact that you are dating your best friend. Any screw-up can cost you your best friend, and you know how painful that can be. If either of you messes up, you’ll be losing both your best friend and your partner. That means double the heartbreak and dealing with the excruciating pain of losing one of the most important people in your life.

Being in a relationship with your best friend means putting the most solid friendship in your life on the line. If things don’t pan out between you two romantically, you cannot just go back to being best friends again. The angst and unpleasantness of a relationship gone wrong will damage your bond.

Always keep this in mind. Remember how important this relationship is to you and make the most of it. Sleeping with your best friend can have its own set of pros and cons. So, take your time before taking the plunge of getting in bed with your bestie.

We’re not trying to scare you into anything, just acknowledging what’s at stake and how important this dynamic is to you can often help increase mutual respect in the relationship. The secret to successfully dating your best friend is to never lose sight of the fact that they’re your besties. This will allow you to value your relationship more.

5. Listen to yourself

Never pressurize yourself in your relationship. At times, people try to be hard on themselves to make their best friend, now partner, happy because they don’t want to lose them. They start sacrificing too much of themselves to keep the relationship going.

I had a friend who was still transitioning from best friends into the boyfriend stage, and when her boyfriend kissed her she freaked out. She wasn’t comfortable but didn’t tell her boyfriend. Eventually, she couldn’t take it anymore and broke up with him.

She still wishes that she had listened to herself and told her boyfriend that she wasn’t comfortable. Things would have been way different. Being romantic with your best friend doesn’t come easy. You have to give your mind time to process the transition in your relationship.

If at any point, you’re not comfortable with the way things are progressing, be honest and upfront about it. Remember, this is your best friend in the world, and you can share anything with them.

6. Plan romantic dates

Movie nights are great, but it’s now time to take it a step further. You two are no longer just friends. You two need to start doing things that couples normally do. Creating some spark is the key to being romantic with your best friend.

Plan a candlelight dinner or a romantic terrace date. It may be a cliché, but isn’t the idea of dating your best friend too? These romantic dates will help bring you both closer as partners and make being in a relationship with your best friend more effortless.

The romantic things you do as a couple don’t always have to be sexual or culminate in sex. Look at these dates as an opportunity to build emotional intimacy in your newfound relationship, taking your bond beyond the realm of friendly bonhomie.

When you’re dating a best friend, it may feel awkward to do the lovey-dovey things at the beginning of your relationship. As you both grow more comfortable with the idea of expressing your love, you’ll also be making sure you grow emotionally more attached.

friends to lovers stages
Romantic dates will help bring you both closer as partners

7. Don’t end up being friends with benefits

Many a time, best friends get this rush of feelings and end up as sex buddies. The guilt tricks them into thinking that it’s love and before you know it, you both are committed. Commitment shouldn’t be a product of guilt or chemistry, but a natural outcome of love and being sure that the person is the one you want to be committed to. If you aren’t sure, put a red flag right there or else you both will end up as friends-with-benefits hiding behind a relationship with no love.

Casually sleeping with your best friend can be a slippery slope. What if one of you develops deeper feelings for the other? What if the other falls in love with someone else and wants to move on? And what if you get trapped in a phony relationship with your best friend for the sake of sex?

There are so many ways this arrangement could go south. So, it’s best to steer clear of the temptation of getting physically intimate with your best friend if there are no real feelings involved. To try and tackle this, perhaps don’t have sex early on in the relationship with your best friend.

Related Reading: Why I prefer friendship over romance with my partner

8. Bask in the glory of love

You both might have known each other for an eternity and been friends for years before dating, but your romantic feelings are new. Let the love and the heady rush of emotions you feel for each other sink in. Tell yourself that this is normal and it’s all going to be great.

Don’t feel awkward about kissing them or feeling sexually aroused by their touch. At the beginning of the relationship, you may find it hard to keep your hands off each other or may want to text each other throughout the day. Remember that these are just normal emotions that couples in a relationship go through.

Once you normalize feeling your heart skip a beat at the sight of your friend-turned-partner, you will be able to transition through the different friends-to-lovers stages faster.

9. Keep in mind their past

Being a best friend, you are privy to the scars of their past. You must have been the first one to know what went wrong in the previous relationship and how bad it broke your partner. Avoid making the mistakes that their ex made.

For instance, if you know that your best friend hates being lied to because a former partner who was cheating on them was dishonest in the relationship, try to be as transparent as possible. When starting a relationship with your best friend, your endeavor should be to cultivate a bond that erases all the pain and agony their past may have brought them.

One of the best things about being in a relationship with a best friend is that you know their triggers and they know yours. Therefore, empathy and consideration will come naturally to you in the dynamic. Keep it as a checklist of all the wrongs that you can right. It will help heal your partner and lead to a healthy relationship between you both.

10. Keep checking on your best friend

Now that you are best friends cum boyfriend/girlfriend, you need to take care of them more than usual. Keep checking on your partner and make them feel cared for. Show them that they are special and this relationship means something to you.

When you start dating your best friend, it’s easy to take them for granted since you both already know how much you value each other. It’s important to care for and love them the way a romantic partner would. Don’t hold yourself back from expressing your love and affection just because it is your best friend that you’re with.

While we’re on the subject, don’t expect them to just know how you feel about them just because this person is your best friend. Be expressive. It will make them feel special and feel that the relationship decision was the right one.

Take, for example, Monica and Chandler from the sitcom F.R.I.E.N.D.S. They basically showed us how to date a best friend without ruining the relationship. By always being considerate to each other’s needs, checking up on each other, and not taking the relationship for granted, they made sure they were always sailing smoothly.

Remember the way Chandler proposed to Monica? Though they were best friends, he knew he shouldn’t take her answer for granted and made sure the display was as romantic as could be. So, take a page out of Chandler’s book and mix in a couple of grand romantic gestures whenever you can.

Related Reading: I’m in a friends with benefits relationship and I love it

We have no doubt these tips on being in a relationship with your best friend will make sure you both don’t end up awkwardly staring at stuff on your dates. Once you manage to hit it off romantically with your bestie, there’s not much else you could wish for. However, if you’re still stuck asking yourself “Should I date my best friend?”, let’s take a look at the pros and cons of it.

Pros of dating your best friend

Dating your best friend could be your romcom fantasy come true. If done right, being in a relationship with your best friend can be much better than what’s portrayed in How I Met Your Mother. The pros of dating a best friend are pretty much endless, as you’ll find out yourself when you take the plunge and jump in with both feet.

If you need some convincing before you jump in, however, Here are some of the key benefits of dating your best friend:

  1. No fear of being judged: You can be yourself and explore your hidden desires without caring about being judged by your partner. This is a person you’re already very comfortable with, so you can delve into the relationship with all your feelings, emotions and fantasies
  2. You will be loved: Your partner already knows the real you and no matter how weird you get, he/she will still adore you. They have seen you cry, nurse a heartbreak, get into fights with your parents, fail and excel in different spheres of life, and have been with you every step of the way. You’ve always known that they’ve got your back. And that’s never going to change
  3. No unpleasant surprises: There aren’t any surprises because you already know the worst parts of your partner. You have probably got drunk and nursed hangovers together, been partners in crime. You have seen them at their highest highs and lowest lows, so there are no unsightly skeletons in the closet
  4. Never run out of things to talk about: Conversations will be never-ending because you both will always have something to talk about. And the best part; no jealousy. Given how important communication is in a relationship, you should count it as the biggest blessing of starting a relationship with your best friend
  5. You trust them: You know your best friend in and out and trust them with your life. Nothing can break that kind of bond. Being in a relationship with your best friend means no struggling with insecurity and trust issues

If the question “should I date my best friend?” has been eating away at you, hopefully, these pros have convinced you to take the leap of faith.

best friends

Cons of dating your best friend

As exciting as it is to date your best friend, every relationship has its cons. When starting a relationship with your best friend, do remember the flip side of this romantic association. Here are some of the disadvantages of dating your best friend:

  1. Dragging the past into fights: Your best friend knows you too well, and they might just bring up the skeletons in your closet when you both fight. This means you can both end up saying hurtful things to each other, which can affect your bond as partners and friends adversely
  2. Lack of space: There is nowhere to hide when it comes to dating your best friend and this, at times, will also not give you space for yourself. Your best friend-turned-partner can become a constant presence in your life and you in theirs, since you’re now playing a dual role
  3. Losing your support system: You won’t have anyone else to talk to when things turn rough in your relationship because your one confidant may now be the cause of it. You won’t be able to discuss your relationship with your best friend anymore, and that means losing out on the biggest support system in your life
  4. No surprise element: Not having a surprise element in your relationship could also be a bad thing. Since you already know each other so well, the excitement of discovering new things about each other may be lacking in your relationship. This can make the initial days of dating somewhat dull and boring
  5. Losing your best friend: The biggest con of dating your best friend is the risk of losing them forever. God forbid, if you both break up, you will not only lose your partner but also your best friend in one go. That can be devastating, to say the least

Being in a relationship with your best friend can be a thrilling and fulfilling experience as long as you both know how to handle your romantic partnership without letting it ruin your friendship. It can be a tricky balance to strike but one that you can achieve with some practice and patience.


1. Is it a bad idea to date your best friend?

No, it’s not a bad idea to date your best friend as long as you both intend to carry on the relationship for the long haul and work to build a romantic partnership without letting it dent your friendship.

2. Do relationships with your best friend work?

Yes, there are so many instances where people have been friends for years before dating and then went on to get married or stay together for life. A relationship with your best friend can prove to be one of the most fulfilling relationships you’ll ever get into.

3. How do you know if your best friend loves you more than a friend?

If you feel that your best friend is behaving differently around you, for instance, you may find them checking you out or paying you compliments instead of endlessly pulling your leg or being a little more protective of you, it could be because they’ve developed deeper feelings for you.

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