Three Dates In. Should The Two Of You Move Forward? Or Not?

Why Did You Start Dating Him in the First Place?

I gotta tell ya that I totally rolled my eyes when I read that one-third of women only agree to go on dates, just so that they can eat for free. That might be "hee hee" on the surface, but how would you feel if you found out that a man was seeing you ONLY so that he could hopefully get some sex out of it at some point? It's never a good idea to use anyone, for any reason. For starters, it puts bad karma out into the universe.

Anyway, the reason why we write so many articles on first dates on this site ("7 Ways to Have an Incredible First Date", "5 Things That Are OK to Require on a First Date", "What to Wear on a First Date", "First Date Rules I'm Not Afraid to Break") is because first impressions are important. It's not just about how a guy sees you and how you see him, it's also about being clear about why you are going on the first date and, if all goes well, you agree to a second and then a third.

There are a lot of people who end up wasting their precious time because they actually desire a relationship while all they are doing is casually dating. And by that, I mean, they are dating with a literal definition of the word "casual" going on—"without definite or serious intention; careless or offhand; passing". So yeah, in order to find out if there should be a fourth date, reflect on why there was a first one to begin with.

Why Do You Keep Wanting to See Him?

He's cute and funny. You have nothing else to do on a Friday night. Your girlfriends are busy this coming weekend. All of these may be the truth about why you are still hanging out with ole' boy, but time, effort and energy are mad precious. Are any of these truly enough of a reason to keep doing it? The answer depends. If all you want to do is fill up space and he feels the same way, carry on. But if you know that you want more than that, after three dates, it's OK to go beyond typical dating conversation. Does he want the same things that you do out of life? Is he looking for a commitment or just a good time? Does he complement the world that you have created for yourself? Do you see clear signs that he will actually improve your quality of life? Is he a wise investment of your time and emotions?

If you are able to answer all of these questions in the affirmative (and remember, some of these answers, you can only come to by asking him, not assuming), then it makes sense to keep moving forward. Just make sure that you're doing so with the two of you walking together rather than you pulling him along (some of y'all will catch that later).

Are There Already Red Flags That You’re Seeing (and Possibly Ignoring)?

It's sad (it really is) that some people are natural narcissists and sociopaths. Because of this, they put forth a lot of effort to remain as charming and "flawless" for as long as they possibly can. But if you're paying close attention and you notice that someone isn't willing to discuss some of their issues or vulnerabilities three dates in, that's already a red flag in my book. I'm not saying that they need to pull out their credit report or tell you about every fight they've had with their ex; I'm just saying that someone who seems too good to be true or someone who seems to be hiding something, usually is.

If you're new to looking for red flags early on in a relationship, I penned some of them here. Aside from those, feel fine putting your eyebrow up if a man isn't willing to discuss his family, friends or past; if you catch him in a lie; if he already shows signs of being controlling; if he's rude or flirty with other women in your presence or if he refuses to talk about his past relationships on any level.

A lot of people are in piss-poor marriages because they ignored flags in the beginning of a dating relationship. Please don't be one of them.

Is a True Connection Being Established?

It's one thing to like someone or to have some things in common (you can do that with a co-worker or your favorite produce person at a local grocery store). It's another thing entirely to feel like you have a true connection with another individual. To me, when there is a surefire connection, they seem super familiar to your spirit, almost from the first exchange of words.

There's more, though. You're both very comfortable sharing the realest parts of yourself. Communication flows with ease. You're both able to challenge one another without feeling intimidated or threatened. There is a profound mutual respect and care for one another. Reciprocity is effortless. You have similar senses of humor. Time together literally flies by. There's an extreme closeness without ever touching. You like the sides that both of you bring out of each other. After a couple of dates, it's crystal clear that you are already becoming fans of one another.

I know this might all sound like a cheesy chick flick, but here's the true reality check about whether or not you are truly connecting with someone after three dates: even if it ultimately doesn't work out on the romantic tip, because the connection—and mutual respect—is so strong, you can still see them being a part of your life regardless. For instance, there is a guy in my life who I used to tell all of the time, "If you're not the father of my child, I could see you being the godfather." That's how dope our connection was.

Not every connection leads to marriage, but some are strong enough to keep people around for a lifetime. Just…differently than you may have expected. That is an article all on its own, y'all.

Are You Both on the Same Page—of the Same Book?

Last fall, I penned an article for the site entitled, "5 Signs That You're in Love (All by Yourself)". If you'd rather listen to a song about this topic than read it, what do you know about the Mariah Carey old school jam "All Alone in Love"? Yep. It's a pretty common phenomenon to be deeply caught up in someone who doesn't feel the same way.

How does something that emotionally extreme happen? When it's happened to me, it's usually been because of one of two things. Either I didn't ask the guy, point blank, if he wanted the same things that I did or, I wasted time with someone who was unresolved when it came to how he saw our relationship; meaning, on Monday, he could see us being together and then, two Tuesdays later, he wasn't sure.

Is a third date too soon for a marriage proposal? In 98.5 percent of instances, yes. But what it's not too soon for us to say, "Where do you see this going?" If he's crystal clear, his answer will be too. But if he's he's dodging and deflecting, either he's showing signs of being a commitment-phobe or being unsure about you. Either way, a man who is looking for a relationship is going to have a pretty good idea if a woman is a good fit, three dates in (ask your male friends, they'll tell you). If the guy you're seeing isn't, I'm not so sure four more dates is going to change his mind.

Time is invaluable and so are you. It's OK to want to be with someone who is a bit more focused and intentional. It's OK to have initial chemistry and still decide to not move forward with someone who wants so much more than that.

Do I sound extreme? Look at it this way—it didn't take him three offers to know he wanted a job he was after, right? My point exactly, chile.

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

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This Is Why You're So Frustrated With Dating

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