If You're Going To Start Dating Someone You Have History With, Remember These 4 Things

Dating is complicated enough when you’re getting to know someone new. Now add in the fact that you’ve had some history the person you’re dating, and it gets even more interesting. Whether you hooked up a few times back in college or went on a date years ago, your previous experiences together are bound to come into play as you enter this new phase of your relationship. So, if you start dating someone you have history with, there are certain things you'll want to keep in mind.

When you have a history with someone, there’s a degree of understanding between you. That means that hopefully, you can relax a bit on those early dates and just be yourself. As an added bonus, there may be no need for awkward small talk because chances are, you already know a bit about each other. On top of that, you may find that there’s a sense of trust with this person. However, if you had kind of a rocky past, you may also have some lingering feelings of awkwardness or regret that can leak into your new relationship.

Dating someone you have history with definitely has its pros and cons. But as long as you’re aware of all the potential perks and pitfalls, you can embark on this new chapter together with confidence. Here are some things to keep in mind, depending on what kind of history you have together.

If You Went on a Date or Two

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Maybe you went on one date months back, and despite the fact that it was hilariously horrible, you’ve decided to give it another shot. Maybe you went on a few dates that were mediocre, and there simply wasn’t enough of a spark to see it through. Regardless, if you’ve already been on a date or three with your new bae, don’t get too caught up in why it didn’t work out last time around.

Timing is everything in relationships, and perhaps there were certain factors impacting your compatibility that are no longer in play anymore. For example, one of you may still have been hung up on an ex or stressed out with work. The important thing is that now, you’re both interested in giving this connection a real shot. While you can certainly use what you already learned about your crush on previous dates to your advantage, try to approach this new relationship with as much of a clean slate as you can muster. The important thing is not why it didn’t work out before, but rather, why it is working now.

If You Had an Off-Limits Crush

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So, you used to have a crush on bae when they had a girlfriend. Or perhaps you were lusting after them while you were coworkers on a tight-knit team at your company. Basically, your new boo used to be off limits for some reason. But for whatever reason, they aren’t anymore. First off, congrats! There’s nothing more satisfying than finally going out with someone you’ve been fantasizing for basically forever — especially when there’s no longer anything holding you back or causing you any guilt or shame about it.

Speaking of which, a crucial thing to work on in this scenario is avoiding holding on to those negative emotions that you attached to your initial crush. You may still have lingering awkward feelings from when you were crushing hard on this person and they weren’t available to you. If you continue to associate those feelings with your bond, they may end up taking a toll on this new relationship. In order to let go of them, it may help to hash them out with your boo. Openly admitting to them that you used to like them back when they were your manager at the office, or dating an acquaintance of yours, may give you a sense of relief, and odds are they’ll be flattered. In fact, you may be surprised to learn that the feelings were mutual. Then, you can focus on your future together rather than getting stuck on any “forbidden fruit” vibes from the past.

If They Were a FWB

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Ah, the FWB relationship. For some, no-strings-attached sex with a trusted friend is ideal at certain points in life — like when you’re super swamped with work or just out of a relationship, and can’t handle anything serious. There’s definitely nothing wrong with having a FWB. But what happens when that person becomes your full-on bae down the line?

There are plenty of perks to this scenario. For one, you already have established a friendship, so you probably have a solid sense of trust, quality communication, and emotional safety, between the two of you. Plus, you’ve already hooked up, so you already know the sexual chemistry is there. All of those things are pretty critical in a relationship, so basically, you have a head start. However, transitioning into a relationship does require some special considerations. The key here is to set some new expectations and boundaries so that you don’t slip back into your FWB ways. What will change now that you’re in a committed relationship together? What will make you both feel secure as you enter this new phase? Openly sharing your needs, wants and concerns will ensure that you and your boo are on the same page. And as a result, that will help to minimize the chances that either of you gets unnecessarily hurt.

If You Had a One-Night Stand

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Whether you met at a bar, on an app, or at your bestie’s house party, if you had a one-night stand or a few random hookups with the person you’re starting to date, that can certainly add a unique layer to your relationship. After all, you’ve already seen each other naked. Maybe you’ve even managed to help each other cross the finish line (*fingers crossed*). But now that you’re pursuing a relationship with this person, you may have some nagging feelings of awkwardness. Will they remember what your “O face” looked like? Is it weird that you’re going on a first date with someone that you’ve already slept with? While I can’t answer the first question, I can clear up the second: No. There’s nothing strange about turning a casual hookup into a relationship. In fact, people do it all the time.

One thing to remember is that you’ve already established that you have sexual chemistry. So now, it’s time to explore whether you have a genuine intellectual and emotional connection. As such, it’s a good idea to plan real dates in the beginning — you know, the kind where you go out in public and experience new things together. These experiences will spark meaningful conversations, and those convos will offer up new insight into your compatibility outside of the bedroom. That’s not to say you have to wait to hook up with your potential bae. It’s up to you when you decide to get frisky again, and there’s no right or wrong timeline where that’s concerned. However, it’s important to make an effort to get to know each other in different contexts as well. That way, you can ensure that your budding relationship has a strong foundation that doesn’t solely depend on mind-blowing sex (not to minimize the value of that factor).

Having a history with someone can also muddle your feelings a bit. Depending on your previous experiences with this person, you may feel like you fall faster for them than you normally would, or conversely, like you’re guarding your heart more carefully. Remember — your history can actually prove to be beneficial to this new relationship you're pursuing. As long as you maintain open communication about your feelings, set clear expectations with each other, and focus on building on the foundation you've already established, you're primed to ensure that your past together only has a positive impact on your present.