Dating Your Best Friend (The Good & Bad) - Cool Dating Advice

Dating Your Best Friend (The Good & Bad)

woman and man dating and are best friends

You’re in a situation that many people find themselves in. It seems like out of nowhere you began to develop feelings for your best friend. It wasn’t like you went out of your way to fall in love with them.

Somehow it happened, and now you don’t know what to do.

Love is a complicated emotion, and it can wreak serious havoc on anyone. Hopefully, you don’t allow falling in love with your best friend to ruin the friendship that you’ve worked so hard to build up.

No one is going to say that it isn’t difficult to walk away from a friendship when feelings start to develop for the other person. Some people can put aside their feelings for the other person, and it’s not a problem for them.


It can become a problem if the person you have a crush on dates someone else. Feelings have a way of getting people hurt quickly, and you’ll become overprotective very fast if they do end up dating someone else.

You don’t want to be in a situation where you are always having to battle your feelings while trying to maintain a friendship with someone who doesn’t feel about you in the same way.

Here we’re going to talk about if you should allow your feelings to blossom or if it’s a good idea to put cold water on your hopes and forget about it.

Remember, dating is a two-way street, and both of you must share similar feelings. If you don’t, then you’ll end up in a situation where you’re always giving more than receiving in the friendship or relationship.

Pros and cons of dating your best friend

As with anything in life, there are both pros and cons of dating your best friend. Let’s first talk about what the advantages are.

You already have a good understanding of who the person is with what they like and dislike.

A large part of the dating process is learning who a person is. It’s about so much more than learning what the person’s favorite food or movie is. You need to discover who the person is and what makes them tick.

You already know so much about your best friend and this part of the hard work is already done for you.

You know if they have a temper, what bad habits they have, and their past relationships. All of this information is important, and it will help you transition from being a friend to being in a relationship with them.

You share a similar group of friends

Friends are an essential aspect of any relationship. The two of you probably hang out with all the same friends. If you date you aren’t going to have to meet a whole bunch of new people. There also isn’t the worry that you aren’t going to like their friends.

Some may think this is an area that’s not so much of a big deal, but it is. Everyone has a small group of people who are around them and it’s difficult when that group becomes too big to manage. That’s not a problem when you date someone who has all the same friends as you do.

You already know their family


If you’ve been friends with them for a long time, then you more than likely know their family. How many awkward dinners have you sat at where you didn’t know what to say to your date’s family?

All of that is in the past now and you can sit at the table without a care in the world. It’s surprising how much of a weight off of your shoulders it is when you already know your future partner’s family.

The hope is that not only do you know their family, but everyone gets along as well.

Here are a handful of cons when it comes to dating your best friend

You’ll lose a lot of friends if you break up

People will take sides after a breakup, and some of those people will side with the person you were dating. If you feel that the relationship will turn into a marriage, then this isn’t much of a concern.

If you’re casually dating and don’t know what’s going to come of it, then you must be concerned that a breakup will cause a rift among your friends.

You will lose friends forever, and it’s going to be painful. So, keep that in mind if you’re considering dating your best friend.

There is no exploratory period

A great thing about dating is that you learn about each other. The learning process is filled with all kinds of fun and excitement. Not as much of that will exist when you date a friend.

You already know what flavor of ice cream they like the best and what their favorite television shows happen to be.

Not being able to discover a person’s likes and dislikes do take a little bit of the mystery that’s exciting about being in a new relationship.

You’ll lose your best friend if you ever breakup

It’s next to impossible to maintain a friendship with someone after you break up with them. If the other person cheated and broke your heart, then trying to be their friend isn’t going to work.

The relationship doesn’t have to end on a tragic note for it to become unsalvageable. You might have such strong feelings for the person that you can’t back away from them. Anytime you see them you’ll have those same feelings, and it’ll be far too challenging to maintain a friendship.

So, you’ve decided to go ahead and date your best friend

Where should you go on your first date?

The first date when dating a friend is different than dating someone you don’t know. You have been out on what many would consider the first date in the past.

Many don’t consider activities done before the first date to be an official date. None of that matters in a sense because now things are different and these are official dates.

You already know what the other person is into. There is more leeway when it comes to what your first date should be like.

In a new relationship, you’ve got to break the ice, that’s not a problem here. The ice has already been broken, and you are onto the next phase.

With that in mind, it’s not a good idea to put too much emphasis on your first date. Go out there and have some fun and leave it at that.

Dinner and a movie make for a good first date.

Go to a restaurant, and talk for a while, take a stroll through the park. You should do something that is like a date.

It’s probably a bad idea to invite your date over to watch TV or something like that. It should be a date, and it needs to feel a little more formal than hanging out in your sweatpants while watching your favorite reality television show.

A trip to the museum, going to a concert, or walking around at the zoo are all great ideas if you don’t want to chat it up at a restaurant.

Do best friends turn into good lovers?

Some people are worried about their quality of love life when dating their best friend. To put it more bluntly, they’re concerned about their sex lives.

Sometimes dating a friend can produce great results in the sack because you’re not so nervous around each other. There are those awkward moments where you don’t know how the other person is going to react while naked.

Being in bed with your best friend doesn’t immediately make those tensions go away, but they can be much less. You feel comfortable around the person, and that causes you to be more at ease.

Performance anxiety is a real thing in the bedroom, and it’s something new couples often struggle with.

You could find that there is much less anxiety when dating your best friend since you are more comfortable around them.

Not everyone will experience this sort of comfort when having sex with their best friend, but it’s not out of the realm of possibilities. It’s highly unlikely that you’ll experience a higher level of anxiety while performing in the bedroom with someone who you’ve known for an extended length of time.

How do you know when your friendship turns into a relationship?

The big problem here is that you might feel something that the other person doesn’t. Are you at the stage where you’re hugging and kissing them? If not, then you have to wonder what the problem is.

If you’re hugging them goodbye, then you can rest assured that on some level, they share similar feelings for you.

Someone doesn’t allow another person to get close enough to hug them if there aren’t feelings bubbling below the surface.

Things will progress, and you’ll notice that the two of you are getting closer to each other. You’re spending more time together, and the closeness of your bodies has changed.

No longer do you sit far away from each other while on the bus. You might sit side by side at a booth in a restaurant now. The two of you are texting as soon as you wake up in the morning.

There are little things that people do that happen when someone is far beyond friends. Your time will be consumed spending it with each other and trying to find ways of being together more often.

Can you turn your best friend into a girlfriend?

Now we’re singling out all you guys who are reading this. The vast majority of those who are having feelings for their best friends will be guys. Why is that? It’s because men have a tough time being friends with a woman.

It’s the same reason why women can work with men and not become attracted to them. It’s much harder for a man to be in the presence of a woman and not want to have some sort of relationship with her.

Yes, that sounds old school, but it’s the truth. Women are much better at being friends with men than men are being friends with women.

If she is your best friend, then you know her better than anyone else. Are you a good match? You must make sure that you’re not dating of desperation or sexual attraction.

If you blow this, you’ll never be her friend again.

A guy usually will not be friends with someone who was his girlfriend after a breakup.

Most guys will be hurt when she has a new boyfriend, and it’s going to cause emotional anguish. If you feel that the relationship won’t last, then don’t pursue it.

You’re asking for all kinds of problems down the line and the friendship will be over. Maybe, more importantly, you’ll end up losing a lot of friends when the two of you split ways.

Sometimes friendships are best kept the way they are

If you’re in doubt, then it’s probably best that you hold off on dating your best friend. It would be far better to have a best friend for life than it would be to be in a relationship that fizzles out.

Dating a best friend can turn into a beautiful relationship that blossoms into a marriage. You won’t be the first couple who started as friends, and you won’t be the last either.

Understand the risks and rewards before getting into a relationship with your best friend to put it all into perspective. If you feel the risk worth it, then give it a go.

Sometimes dating your best friend isn’t as thought out as the words are in this article. Some day you may wake up and realize you’re in a relationship with your best friend.

The relationship formed out of the blue, and neither of you put any thought into it at all. The relationships that have the highest success rate amongst best friends are those that happen seamlessly.

You don’t know when the relationship began, you only know that you’re in a relationship when both realize it’s not possible to live without the other.

Date night ideas to have some fun.

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