The Pros and Cons of Dating Your Best Friend

Dating your friend’s ex can be tricky. Dating your ex’s friend can be even worse. And dating your friend? Well, that’s a whole other ballgame. But if you’ve ever wondered “what if” when kicking it with your best pal, you’re not alone. After all, there’s a reason you love being around one another so much. And we’re not talking about just any old pal here — this is the person who makes you laugh harder than anyone else and is always on your mind.

If your best friend is the one person who truly gets you, it may be time to consider making it official. Here are 10 pros and cons of dating your best friend.

1. Pro: They’ve already seen you at your worst

Portrait of upset young woman

Best friends are there through the best and worst of times. | iStock.com/JackF

The thing about best friends is they know each other inside and out. You’ve argued over politics, religion, and family stuff. You’ve shared your world views and established the points you agree, and disagree, on. So, it’s safe to say your best friend has also seen you at your worst.

This is a bonus for the both of you, considering there will inevitably be disagreements aplenty down the road.

2. Con: You’re all too familiar with their flaws, and you can’t get over them

man chomping on a carrot

There’s no escaping their worst flaws now. | iStock.com

When you were just friends, you could safely cut back on the amount of meals you ate together if you couldn’t stand his or her eating habits (nobody likes an open-mouth chewer). But now, there’s no running from shared meals. You’re together, and you’ve quickly realized just how frustrating their nuances really are. Will you be able to suffer through it much longer, or will you have to jump ship?

3. Pro: You already have the same group of friends

Group Of Friends Enjoying Night Out

Having the same friends is definitely a plus. | iStock.com

Introducing a new partner to your inner circle can be tricky, unless of course, you happen to already share the same group. As Romper points out, introducing a new significant other to your friends can be a process. But if the two of you were best pals before? Well, it’s likely you already have the same group of friends, which makes adding events to your social calendar a no-brainer.

4. Con: If you eventually break up, you could cause a rift in your circle of friends

friends drinking beer together

Will your friends be forced to choose sides? | iStock.com

It’s a tale as old as Ross and Rachel. The only exception is, you probably don’t have the safety net of a rent-controlled apartment to fall back on. The trouble with sharing a bunch of mutual friends is that you could end up losing some if things go south. Now of course, we’d never wish a terrible breakup on anyone, but it’s always a possibility. And if you and your partner eventually decide to call it quits? It’s likely some friends will feel as though they need to choose a side.

5. Pro: You may already know their family

grandparents with grandkids

Lucky you, you already know their parents and nieces and nephews! | iStock.com

Meeting the parents can be a daunting experience. After all, there’s an entire comedy devoted to the gut-wrenching task of meeting the folks. But perhaps your experience won’t be as bad as Ben Stiller’s. Maybe, just maybe, you won’t be tasked with having to meet your significant other’s parents for the first time at all … because you’ve already met them. In fact, you know the entire family, from parents and siblings to nieces and nephews. Its’ pretty much a dream come true.

6. Con: You already know their family, and you’re not too fond of one another

friends having a good time at a holiday party

Maybe you got a little too loose at last year’s family holiday party. | iStock.com

On the flip side, maybe you’ve already met your best-friend-turned-significant-other’s parents, and maybe you’re not all that fond of them. Or, perhaps they’ve not seen you in the best possible light.

When you meet a partner’s parents for the first time, you’re typically on your very best behavior. But what if you met your friend’s parents during a wild graduation weekend? Or at a wedding when you were dating someone else and going a little too hard on the PDA? Even if this kind of behavior is in the past, it could end up backfiring if you’re not careful.

7. Pro: You don’t have to suffer through an awkward first date

Couple riding bicycles in the city

Your first date was the best. | iStock.com/gpointstudio

Everyone’s had a bad first date. But when you finally decide to call a dinner with your best friend more than just a dinner with your best friend, there’s no need to stress about first date awkwardness. You’re not worried about saying the wrong thing, yet you still have those butterflies that come along with any first date. It’s pretty much a win-win.

8. Con: Your first date doesn’t actually feel like a first date

men clanging glasses of alcoholic beverage

Maybe it’s a little too casual for your liking. | iStock.com/GeorgeRudy

Here’s the one issue with finally agreeing to go on an official date with your best friend. It could end up not actually feeling like a date at all. Despite the fact that you both got dressed up and headed to a nicer place than usual, it still feels like you’re eating wings at your favorite sports bar. This, of course, could be a blessing in disguise, because at least you might get the inclination right off the bat that you’re better off as just friends.

9. Pro: You don’t have to worry about dressing to impress

young couple visiting eat market

You’re comfortable around one another, and that’s what matters. | iStock.com/nensuria

When you have a crush on someone brand new, it’s not uncommon to fret over looking your best. When you have a best friend, on the other hand, you’re typically not too concerned about being able to slip into your skinniest pair of jeans. In fact, you don’t think twice about donning your favorite pair of comfy sweats and going braless. Gone are the days of spending hours trying to decide what to wear. You’re comfortable together, and that’s wonderful.

10. Con: You’re a little too comfortable in front of your new partner

man kicking up his feet to nap on a coach

Don’t give up on making a good impression too soon. | iStock.com

There’s something to be said about those butterfly moments during the honeymoon phase of a relationship. You’ve already crossed into the relationship zone, but it’s still fairly new. And depending on how you’d like the relationship to progress, being a little too comfortable may not be the best thing in the world. Even though the two of you were best friends first, most relationships thrive on the novelty of it all. So, maybe reconsider letting it all hang out 24/7, at least for a few months.

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