Dating your Best Friend
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Should You Date Your Best Friend?

Should you date your best friend?

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Who hasn’t asked themselves that question at some point in their life?

It’s no secret that the best relationships are built on a foundation of friendship. If you’ve been to a wedding, you’ve likely heard the bride and groom talk about how lucky they are to be spending the rest of their life with their best friend.

Which brings us to the very important question of what comes first the friendship or the romance? The chicken or the egg?

There is no shortage of opinions on both sides of this matter.

To date your best friend or not to date your best friend, that is the question. Sometimes it is the biggest question.

It’s the question I came back to time and time again as I read Emma Hart’s new book Tequila, Tequila. It’s a wonderfully quirky tale of two best friends who find themselves in bed together after a few too many drinks.

Read the Book that Inspired this Discussion: Tequila, Tequila by Emma Hart

Luke and Aspen have to think long and hard about where to go next. Is a relationship between the two of them is worth a shot? Does it even have a chance of success? Are the potential costs of a failed relationship worth the potential rewards?

Tequila, Tequila considers many points both for and against a relationship. Let’s look at what some of them are.

We will get through both sides of this predicament. And we will do it in the most logical way I can think of. If you’re trying to figure out whether dating your best friend is a good idea you’re probably not dating them, yet. Which means we’re going to start with the arguments for maintaining the status quo.

So without further ado,

Why You SHOULDN’T Date Your Best Friend

You Could Lose Your Best Friend Forever

This was a big one in the book. Is a potential happily ever after worth risking one of the most meaningful friendships in your life? What happens if things go wrong. Once you cross the line into relationship territory, you can’t just cross back. It’s hard when you have to cut ties with a friend, it’s hard when you have to break up with a partner, doing both at the same time could be unbearable.

You Know Each Other *really* Well

Let’s be honest here, does your best friend know anything you wouldn’t want your significant other to know? My bestie certainly does! Best friends know your deepest secrets, they’ve been with you for a long, long time.

I’m not saying keep secrets from your partner. But my best friend knows about those things because he was there with me through most of them. My hubby knows them because I shared those things with him. Two very different situations.

You’re a Little Biased

You know those red flags you notice in the early stages in a relationship? In the beginning of a relationship people are careful, they’re projecting their best self. On a first date you’re getting dressed up and going to nice restaurants, when you’re hanging out with your best friend, you’re wearing yoga pants, watching Netflix and eating pizza right from the box. You know they’re amazing and you don’t look at them the same way you would a potential partner you’re getting to know. Sometimes friends don’t make good romantic partners.

Are you Getting into a Relationship for the Wrong Reasons?

It’s convenient. You care deeply about each other, otherwise you wouldn’t be friends. You know each other, there’s no need for awkward small talk. It’s comfortable. I’m not even going to talk about this, convenience is probably not a great reason to fall into a relationship.

Blurred Lines and Differing Expectations

Relationships are messy, full of disagreements. Did I mention, they’re messy? One thing I have always been able to count on is the fact my best friend will take my side in a disagreement with my spouse. If I’m having a disagreement with my spouse who is also my BFF, they’re obviously not going to take my side in the matter. See, messy, just like I told you!

Who do you Turn to When You Need Someone?

No one goes into a relationship planning for the breakup, but best friends are essential to break up survival. When your best friend is on the other end of the failed relationship you can hardly expect them to show up with chocolate and ice cream, can you? You no longer have access to a most treasured resource. Aspen and Luke had a third best friend, which I guess made things better, but my goodness the poor girl would be in a bad place if they had a messy breakup.

Related: Best Friends to Lovers Romance Novels

Why Your SHOULD Date Your Best Friend

No Awkward First Date

Your best friend knows things about you. A lot of things you might wish no one was privy too. But aside from that they know your favorite color, the foods you absolutely hate, you strange pet peeves, even your political and religious views. The best part is they still like you, which might be more than you can say for the last several people you tried to date.

You don’t Need to Own Up to any Disastrous Dating Mishaps

Luckily, as your best friend they were there for the worst of the worst relationships you’ve had. Meaning there’s no need to recount those disastrous ‘experimental’ years or the time you realized your partner had a wife and kids you didn’t know about. Speaking about secret lives, you can be pretty sure you best friend isn’t hiding anything from you, no way anyone would make it all these years without slipping up.

They’ve Met Your Family

And didn’t run away screaming. In fact, your parents probably even approve of them. Again, likely more than you can say about the last several partners. If you’re like Aspen and Luke your parents so strongly approve they’ve offered to marry you off to their cousins and siblings. They want you in their family. Plus, you get to skip the immensely awkward meeting the parents part of the relationship.

They Know All Your Quirks

Believe it or not, your family might not be the most embarrassing thing about you. They know so many things about you. From your aversion to watching movies with socks on, or the way you eat peanut putter straight from the container. They know all those things, and like you anyway. Let’s face it, not all potential partners will be so understanding.

You’re Both Invested

There’s no way you go into a relationship without you both knowing what’s on the line. I mean, whether or not you admit it, you know your friendship will change and if things go wrong, you likely won’t ever be able to go back to the way you were before. This isn’t a reason not to enter a romantic relationship, it’s an incentive to make sure the relationship works out.

You’ll Always Wonder

Once you straddle the line between friendship and more, you ask yourself certain questions. You mind wonders places it really has no business wondering. Before you know it, you’re comparing every future relationship to what you assume your best friend will be like in those situations. You’re holding all potential partners to an insanely high standard. Your best friend is awesome why would you expect less from a partner?

Speaking of wondering…

I bet you all want to know what happened to the couple in the book. You will have to read it and find out.

Final Thoughts

Well, there you have it, several reasons you should or shouldn’t date your best friend. Unfortunately, I can’t tell you what to do. The final decision is all up to you. Weight the pros and cons, consult your feelings, talk to your mom, flip a coin – whatever you do, you’re on your own with this one.

Deciding to enter a relationship with someone probably isn’t a decision that should be taken lately. That’s doubly so when that person is your best friend.

Whatever you decide will be the best decision for you. Good luck! 🙂

Perhaps a few awesome Friends – to – Lovers romance novels will help you figure things out. I recommend: Marriage Lessons or Hard to Resist

Let’s Talk

Have you ever fallen down the rabbit hole of dating your best friend? How did it go? Did you get your happily ever after? I hope you did! Are you thinking about it? Tell me all the things. There’s nothing I love more than a good love story.

As Always,

Love, Sawyer Logo

Dating your best friend


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