Dating a Friend You've Known For Years

How To Start Dating a Friend You’ve Known For Years?

by John Santana

Do you remember that moment in “When Harry Met Sally,” when Billy Crystal’s character explains the old riddle of male and female friendships? He tells Meg Ryan that “men and women can never be friends because the sex part always gets in the way.”

The saying is somewhat correct. At some point in time, you may be physically attracted to your friend and want to change the status of your relationship to something more than just being friends.

In all honesty, dating a friend is widely seen as a pursuit filled with potential complications. If it works out, fantastic, but if it doesn’t, then it’s very likely that your friends will turn sour.

If you are in that position right now, where you are considering dating a friend you’ve known for a long time, then you have come to the right place.

In this guide, we break down the pros and cons of dating a friend and share some helpful relationship advice.


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What Are The Benefits Of Dating a Friend?

There are endless benefits to dating a friend. We have highlighted some of the things you may enjoy if you become romantically involved with your friend.

You Already Know Each Other

One of the most annoying parts of dating new people is that you have to re-introduce yourself and explain your entire life story. It takes a lot of time to get to know someone and grow comfortable enough with them to share your personal memories and secrets.

Dating a friend means that you can eliminate this frustrating phase. You both know each other so well and are already comfortable with each other. Your friend knows your favorite color, food, place, etc., but most importantly, they know your insecurities and deepest, darkest secrets.

To have a successful and fulfilling relationship, it’s important to know each other’s weaknesses. When you’re dating a friend, you are already aware of each other’s shortcomings, so you know which areas you can help them with.

When you date a friend, you are already familiar with their ambitions, and you’ve probably given them tons of advice on their career path and vice versa. You already know what you both are aiming for, so you can work towards your goals together.

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You Can Talk To Them Like a Friend

Dating a friend means that you’re comfortable enough to talk to them freely. They are basically your walking diary. There are no formalities, restrictions, or thinking twice about whether it’s an appropriate conversation to have with them.

You can tell them anything that makes you sad, angry, nervous, happy, or scared. You can confide in them without worrying about being judged. They’ve been there for you your whole life or at least a major chunk of it. You know you can be vulnerable with them and they will be there for you.

You Have Already Established Shared Interests

Friends are often friends because they share a lot of similarities. Dating someone you are friends with means that you already have plenty in common, including shared interests. This is one of the biggest advantages of dating a friend. For example, if you both already know you love horror movies and prefer a night in rather than a night out, you don’t have to go searching to find something in common.

Most people are physically attracted to others in the dating scene but are poles apart when it comes down to their interests. Physical attraction is important, but if they prefer the adventurous outdoors while you enjoy luxury treatments at the spa, then it may not be a good match. Knowing that you and your friend have a mutual fascination can give you guys the upper hand in this area.

According to psychologists, couples who share the same interests often have healthier, longer-lasting relationships. Shared passions also reduce the amount of fighting between couples when it comes to topics like finance. Common interests between friends are just as important as those between romantic partners.

You Both Know Each Other’s Families

When you are in a committed relationship, meeting each other’s families plays a very important role in determining the success of your relationship. A relationship is so much more than two people being just in love with each other because families have to give their approval too.

Dating a friend means that this aspect is already covered. It is very likely that your friend already knows and is comfortable with your family and vice versa. Chances are that their family could even have been waiting for them to introduce you as their new partner. If you are not the type of person that they would like their child to be associated with, then you have already been given the cold shoulder.

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You Both Are Part Of The Same Social Circle

Dating someone who is your friend means that they have already spent quality time with you and your mutual friends. This is a huge benefit because it means that they fit into your social circle.

Many couples encounter uncomfortable situations where one is disliked by the other’s friends, which can result in bitter resentment. Knowing that you and your new partner already enjoy the company of the same people automatically solves this problem.

According to psychologists, couples who spend time with the same group of friends have a higher chance of experiencing satisfaction in their relationship.

They Already Know About Your Past Relationships

When you decide to date a friend, you already know everything about their past, including what their exes looked like and why their past relationships never worked out.

Because your friend was there the entire time, comforting you, you don’t need to relive your past or explain why you don’t like certain things. They know what went wrong and understand your fears.

Them knowing this private information can strengthen and create a closer bond between the two of you.

They Are Always Available To Hang Out With

When you are dating someone other than your best friend, you cannot guarantee that they will be available to hang out all the time. You may be hesitant to invite them over regularly because you are concerned that you will inconvenience them.

But with your best friend as your partner, you will know for sure that they will readily make themselves available for you and won’t feel suffocated by your presence. They will enjoy hanging out with you just as much as you do with them.

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What Are The Challenges Of Dating a Friend?

Couple together

When you decide to turn a platonic friendship into a romantic relationship, it can be a lot of fun. But certain challenges come with dating your friend that you should be aware of. We have outlined some of the potential pitfalls of dating a friend.

Lack of Excitement And Surprises

Dating someone with whom you are already good friends can be a wonderful experience. But because you both know each other inside and out, there may be very little to look forward to.

Often in a new relationship, there is initial excitement and suspense, which encourages couples to give their best. When you’re dating someone you know so well, it takes away the element of excitement and surprise. There is nothing left to spice the relationship up, which can feel very mundane and boring.

If you want to form a romantic relationship with your friend, then you need to accept that this element is gone. If you can’t find a way to resolve this issue, then it may be a better idea to just remain friends.

Familiarity Can Create Contempt

You cannot deny that because you are best friends, you may not take each other seriously. Your friend might even think that you are joking when you bring up the dating idea. You may find yourself having to repeat things to them just to convince them that you are serious and not joking.

Likewise, when it comes to respect, you may be a little disappointed when dating your friend. You may not get the kind of respect that you want from a partner from your best friend. They are someone who knows you so well that they have little or no reason to be afraid of you.

There Is No One Else To Discuss Your Relationship Issues With

Previously, when you had problems with your parents, siblings, or partner, you could go to your best friend to discuss it and get some advice. But if you are dating your friend, you won’t have anyone else to turn to when you face issues in your relationship.

In a way, this can be a good thing because you keep your relationship problems internal and don’t seek out advice from or involve third parties. But sometimes you may not be able to avoid this. In this kind of situation, having no one to turn to is not a nice thing to experience.

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You Could Risk Losing Your Friendship

When dating a friend, it’s important to remember that you could lose them forever. If for some reason the relationship fails, then it’s likely that your friends will too. This is probably the biggest downfall when dating a friend.

No one enters a relationship thinking that it will fail. Many people start dating someone with the hope that it will last forever. But in real life, two people can grow apart.

When you and your friend start dating, you may share similar interests and plans for the future. But as time passes, people change. Everyone has the right to evolve, which means that they can outgrow the other person. If this happens, the relationship will most likely not last.

If the relationship ends, you need to be prepared to lose your friend forever. After a breakup, either one or both of you may choose to no longer be friends because of any painful emotions that may still be there.

According to a dating expert, rekindling a friendship after a breakup is only possible if both people no longer have any intense emotions lingering.

There May Be a Situation Of Unrequited Love

If you have a crush on your friend but your feelings are not reciprocated, it can result in an uncomfortable situation. But if you share a mature, solid friendship, then this kind of awkward tension won’t last long or may even not exist at all.

It’s not an easy thing to remain friends with someone who you are romantically interested in but who has rejected you, but if the friendship is worth it, you will make it work. Think about how amazing your platonic friendship was with this person before you confronted them about your romantic feelings towards them.

You may even decide to take a break from spending time with this one friend. Psychologists suggest journaling, exercising, and going to therapy to help move on and heal.

Should a Breakup Happen, Mutual Friends May Feel Divided

If you end a friendship with someone with whom you share mutual friends, it can create a division among everyone who is involved.

Your friends may naturally assume that they have to choose who they can remain friends with once everything is done and dusted. The ideal way to handle this kind of situation is to reassure your friends that they don’t need to cut anyone out. Everyone can spend time with whoever they want to.

Don’t be the bad guy and force your friends to pick between you and your ex. That’s emotional blackmail and unfair to your group of friends.

If you and your ex have ended your relationship and no longer want to spend time in the same places, then you both need to see how you can maintain strong connections with your group of friends without having to bump into each other.

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Things To Consider Before You Decide To Date a Friend

She Locks Eyes With You

If you are thinking of dating your friend, there are a few factors you should take into consideration before jumping into a romantic relationship. These factors will help you determine whether you have a better chance at being romantic partners or if it’s best for the both of you to stay just friends.

Check If There Is Mutual Attraction

It can be difficult to tell if you and your friend have mutual attraction and feelings for each other when you are already so sweet and friendly to each other. A good way to test the waters is to flirt. This will not only protect you from rejection, but it will also create a safe space to see whether the other person flirts back.

It’s important to take your time and gradually get more flirty. This will help you check whether they return the flirtiness or if they are only flirting with you and not everyone else.

According to a dating expert, here are some signs of a mutual crush:

  • The person is looking for more opportunities to spend time with you, and it is happening even outside of your friend circle.
  • They are beginning to share more personal information and intimate details.
  • Their body languages, such as touching and eye contact, and opportunities to be physically close are increasing.
  • They are eager for you to meet their family.
  • They flirt with you and give you compliments.
  • They get jealous or possessive when other people want their attention.

Make Sure You Have The Right Type Of Friendship For a Relationship

There is a significant difference between your best friend and someone with whom you enjoy partying. A relationship psychologist advises that you first consider the quality of your friendship before progressing to a relationship.

You need to think about whether you feel safe and secure in that friendship or if it is just an exciting emotional rollercoaster.

Be Honest About Why You Want To Date Them

Dating a good friend may seem like a great idea. They are always there for you, they make you happy, you can trust them, and they will never hurt you. But a healthy romantic relationship is so much more than just feeling secure.

There needs to be a romantic desire or some type of sexual attraction. Even if these elements are present, they may not be sufficient for a healthy, long-lasting, stable, and romantic union.

When it comes to shared goals and parallel life plans as well, sometimes dating someone who feels safe can be a bad idea because they are not as motivated or socially interactive as you.

In The Beginning, Don’t Involve friends

When you realize that you have mutual feelings for a friend, you may feel that you need some help getting through this. But if you are going to talk to someone, consider choosing a person who isn’t part of your mutual friends.

Shared friends may be psyched about this new romantic partnership, but at the end of the day, a romantic relationship is between two people.

Understand That Your Relationship Will Get More Challenging

When you start dating someone with whom you previously had a close friendship, you should expect things to become more emotionally complicated than they were before. The two of you need to work together to create a new sense of commitment and interdependence.

In romantic relationships, people are more dependent on one another than they are in friendships. You’ll need to figure out how to deal with jealousy, combine your schedules, and support each other through bigger life problems.

Final Thoughts

Friendships that turn into romantic relationships are some of the best relationships. But, like with every type of relationship, it’s important to weigh the pros and cons before just jumping straight in.

We hope that our guide will help you navigate through this situation with ease.

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John Santana

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