Do You Both Want to Take Things Up a Notch?

Perspective is everything. This is definitely the case when it comes to dating. I've shared before that I once had a birthday dinner with a guy. During the dinner, he proceeded to tell me that he was "dating me", along with a whole lot of other women. Yes, he was narcissistic (LOL not LOL), but that's not why I'm bringing this up. I'm saying it to say that this is a great example of the fact that while one person may think a date is just good company over pasta and wine, another could be thinking it's three dates away from forever (or whatever ole' boy was arrogantly talking about).

That said, if you and a guy have been on more than three dates, there is something there. But your "something" may not be "his". So, if you want to go from just hanging out to hanging-out-with-the-intention-of-it-maybe-becoming-more-someday, that's a conversation that needs to be had; not just in your mind or with your girlfriends, but with him too.

The good news is if he's even entertaining the discussion of, "How do you feel about being a little more than hang out buddies?", he's interested beyond just being around you to have something to do. If he shuts it all down, well, he's not only not open to seriously casually dating, you may have some ghosting ahead in your future as well. Just sayin'.

Are You Cool with You Both Still Seeing Other People?

Here's the thing about dating. Just because you are doing it with someone, that doesn't automatically mean that exclusivity is—or even should—be on the table. I often say that a lot of folks have a tendency to think that chivalry and courting are synonymous although they absolutely are not. I don't care what kind of dating status you are currently filed under, you deserve for a man to treat you with respect and care; however, if a man is courting you, by definition, he is intending to marry you (not because you assumed it; he actually told you so). On the other hand, if he's just dating you, that could mean that he likes your company, along with the company of five other women. Or, that he's trying to see if you are someone he wants to be with, long-term.

Category B is a lot more serious than Category A. So yeah, if the two of you are considering entering into serious casual dating territory, something else you both should get clarity on is if you're both OK with the other seeing other people. Honestly, if it's only on the seriously casually dating tip, this shouldn't be that big of a deal.

Is Sex on the Table?

If the two of you like spending time with one another to the point where you're going on at least a couple of dates a month, an emotional connection is going to be established; that's just how life is. And, by the second month or so (at the very latest), you're going to become more physically drawn to one another as well. This means that another thing you need to think long and hard about is if you want to get sexually involved or not.

Out of all the things that we've touched on thus far, this is super important because, if the two of you aren't going to be exclusive but you are open to having sex (oral or otherwise), you could be putting yourself at risk to contract, whatever his other partners may have (whether they know it or not; remember, most people with an STD have absolutely no clue that they do!).

This is why, even if you are down for seriously casually dating, you might want to rethink how "casual" sex ever really is (spoiler alert: it ain't).

Do You Have Realistic Expectations?

I don't know about you, but it's been my personal experience that—both on a romantic and platonic level—men are pretty literal. As it relates to what we're unpacking here, this means if both of you agree that you're both going to see each other and other people, they are not gonna try and see if you have some sort of other agenda in mind. Agenda like what? Something like, "I'll tell him that I'm fine with him dating other folks, but I know that if we spend enough time together, eventually he's gonna leave the others alone and want to be exclusive with me." Could that happen? Lots of things could happen, but don't bet on it going this way just because you want it to.

This point reminds me of a situationship that I once had with a guy many moons ago. Because my self-esteem was not where it should have been at the time when we met, I put a wall up and said that I was cool with being friends with benefits, nothing more. After months of sex, phone calls and even a pregnancy, I figured that since we had been through so much together, surely, we had a future. What he said in response to my mindset has always stayed with me. "Shellie, you never gave me a chance to see you as more. When you said you wanted to stay friends, I took that to mean just that. So, I've always only seen you that way." Ouch. He was right to process us that way, though.

It reminds me of a man by the name of Mark Gungor who once taught the difference between men's minds and women's minds. He said that men think in boxes (everything is compartmentalized) while women think with string (everything is connected). If you do decide to enter into a seriously casually dating situation, watch that video and then decide if you can realistically handle doing that.

Because many a man can like you, sex you and that be it while you're somewhere thinking that everything is tied in together to mean something more. Maybe. MAYBE NOT.

How Much Should (and Shouldn’t) Be Discussed?

This is a super valid point too. Just because you both have decided to be open about seeing each other and other people, that doesn't give either one of you the "right" to know about the other individuals. You know what else? If neither of you want to discuss the other relationships, that also doesn't make either of you sneaky, shady or someone who lacks integrity or respect for what the two of you share.

You probably know all of this from an intellectual standpoint, but once emotions and possibly sex come into play, it can still do a real number on how you process things. So yeah, if you do decide to seriously casually date, it's a good idea to set a few ground rules about what is cool to talk about and, what both of you would prefer to keep off limits. At least for now.

Besides, if the two of you are keeping it relatively casual, why should either one of you be digging into the other aspects of your dating life anyway? (Hmm…)

Is There an “End Game” in Mind?

I remember once watching a television show and one of the characters on it saying, "With time, everything exhausts itself." If you don't tend to and nurture it—whatever "it" may be—I totally agree. Whenever I ask my 39-year-old friend about how her seriously casually dating situations end up, typically, they don't end well. Someone catches stronger feelings or has a different set of expectations. Or, one or both come to the conclusion that what they were doing was a total waste of time.

This doesn't have to be the case for you, but it is a good idea to always keep in the forefront of your mind that casual means "without emotional intimacy or commitment". If you want to spend months of your life without a commitment, have a ball. But if even a little part of you wants something different, be real with yourself about that.

Seriously casually dating only works if both people honestly want it to. Otherwise, it brings unwanted drama into one's life. And really—who wants that?

Want more stories like this? Sign up for our newsletter here and check out the related reads below:

The Things Men Say On Dates That Are Huge Red Flags

15 Date Ideas Based On Your Love Language

Here's Why You KEEP Not Getting What You Need In Your Relationships

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