1. “How would a relationship benefit you at this stage of your life?”

Wanna know how a lot of us find ourselves in full-on relationships with commitment-phobes? It's pretty simple, actually. If we meet a guy who checks all of our boxes, we have a really great time with and the chemistry is totally off the charts, we can oftentimes assume that this special combo is the foundation for something long-term. But here's the thing—if he's not looking for anything serious, he can feel the same way and still never intended on building a future with you.

As a marriage life coach, I can't express enough, just how much assumptions can damage, if not flat-out ruin, a relationship. So, if you've been seeing a guy for a hot minute and you can tell that you are on the road towards getting pretty attached, it's a good idea to ask him something along the lines of, "So, a relationship. Is that something that would fit well into your world right now?" If it is, he will absolutely have no problem expressing that. If he looks at you like you're out of your mind, well, that's an answer too. Bottom line, people who are open to a relationship are not afraid of the word or a discussion about the word. So, if it's been three dates or more at this point, don't feel like you are being pushy or "needy" by broaching this topic. To a mature man, you're not. Not at all.

“Do you feel comfortable enough to share your vulnerabilities with me?”

I've shared in articles for married folks that I'm not big on using the word "vulnerable" in that kind of relationship; I prefer the word "dependent" instead. The reason why is because, if someone has stood before God, their mama and their partner's mama to profess that they will hold them down like no one else can (or should) for the rest of their life, they shouldn't feel like they are being vulnerable (capable of or susceptible to being wounded or hurt, as by a weapon; open to moral attack, criticism, temptation, etc.; open to assault) with that individual. Nah, being dependent (relying on someone or something else for aid, support, etc.) is much safer. Healthier too.

If there's one thing that a lot of men—especially Black men—tell me is, they have a really difficult time feeling like it's OK to be dependent in their romantic relationships because their partner is very much into morally attacking and criticizing them. Or worse, their partner will say, "You can tell me anything" and then when they let their guard down and do it, they get denounced for it.

I don't care how beautiful a woman is or how good her "stuff" may be, if her man can't feel completely comfortable being his full and total self with her, she's in a surface-layered relationship; one that oftentimes has an expiration date. So yeah, if you want to get to the next level with someone, asking them if they feel like they can talk to you about, pretty much anything, is a very valid question. Make sure you listen very closely for the answer that they give you. It will reveal a lot.

3. “What are three things you wish you could do over from your past relationships?”

It's pretty much human nature that, if you ask a person why their last relationship ended, that they will go on and on about all of the things that their ex did wrong. That's why I give major points to those who are humble and self-aware enough to own their own ish because, 8.5 times out of 10, everyone plays a significant role into why a break-up transpired. Besides, when you're dating someone new and they are willing to take responsibility for their actions (or lack thereof), you can get some real insight into, not just their areas of weakness and how self-perceptive they are, but what you could possibly be in for should you choose to continue seeing them too.

While it might initially seem awkward to ask someone to share all of their relational faux pas, so long as you are willing to do the same, it honestly shouldn't be that big of a deal. Just make sure to not try and "lead their narrative". What I mean by that is, if he says something along the lines of, "She had a hard time trusting me", it's not a good idea for you to immediately follow that up with, "Oh, so you cheated" like you are accusing rather than inquiring. Being a poor listener is another reason why so many relationships end up going off the rails. Let him tell his own story. Then decide if his missteps are ones that you can handle or not. This question is not about you serving as the judge and jury of his past. All you need to determine is, if once you discover what happened in former relationships, can you hang if similar things just happen to manifest in your relationship with him down the road.

4. “What do I bring to the table that no one else in your world can—or has?”

Something that time and experience have taught me is, I can't stand flippancy. When it comes to this particular topic, a flippant man is someone who would give forth the kind of energy that conveys, "You're really cool and all, but I wouldn't exactly say that you're exceptional." You know what I mean—men who take on the "there's a ton of fish in the sea" attitude. The reality is there are tons of attractive, smart and funny people in the world. Live long enough and you'll get that a great sex partner ain't that hard to find either. So, what keeps two people together for the long haul? It's when they both find something (or a series of things) that stand out in their partner to the point where they really can't imagine being without them. It's kind of like that bun and special sauce on the Popeye's chicken sandwich; while you can find a chicken sandwich a lot of places, those two things are unique in their own way.

That's why this question makes the list. If you can sense that a guy is really feelin' you, ask him why. Not in a I-need-a-ton-of-compliments-and-reassurance-all-of-the-time kind of way, but more coming in the direction of, "So, what do you think I can bring to your life?" or "So, what makes our connection different?" What he says will reveal a lot—a lot about how he sees you and what he desires for the relationship, moving forward.

5. “Do you think that we are capable of meeting each other’s needs?”

Another reason why many relationships don't go the distance? They are way too focused on getting what they want rather than what they need from their partner. Not that wants are a bad thing (not at all), but they should be seen as the icing, NOT the cake. The literal definition of a need is "a requirement" and "something deemed necessary". When something is necessary, it's essential. When something is essential, it's "incapable of being disregarded". While you might want a tall man (girl, I totally get it), you may need someone who is proactively attentive. This is why it is so important to know what your needs are, even before you start dating someone. If you're not sure, you could meet a man who's fine, charming and sexy AF and then "edit" what your needs are, just because you want him so bad that you will overlook legitimate needs just to keep him around.

Once you do know what you need and it seems like a new guy could possibly provide you with those things, make sure by opening up the door to discuss what both of your needs are. Make sure you express something similar to what I just said about needs—that they are pretty much relational deal-breakers if you don't get them. Allow him to share the same. I can't express enough that both of you need to be really frank and candid about if you can meet each other's needs or not. If you can, this is sho 'nuf a sign that you very well are headed towards hitting a new level in your relationship.

6. “What does ‘next level’ mean to you?”

You know the old saying—"There are levels to this." Indeed. Since poor communication—including making assumptions and only hearing what one wants to hear—runs rampant in so many relationships, it can also help to 1) understand that relationships rarely leap from one stage to another (baby steps are the usual norm), and 2) the "next level" to you might not necessarily be the same way he envisions the next level to be. For instance, while you might think that casually dating's next level should be becoming exclusive, he might say that the next level is introducing you to some of his peeps or seeing you more than a few times a month.

When it comes to moving forward with a man, if you want to spare yourself a perpetual feeling of "WTF?!" six months from now, when you're having a next level convo, just so that you can be clear about where things are, make sure he expresses what the next level would look like to him. This isn't a right or wrong debate; it's simply something to make sure that you both are, not just in the same book but hopefully in the same chapter and even on the same page. Because, after all, a healthy relationship consists of two people who are willing to walk together. That can only happen if they are going the same direction and at the same pace. Make sure that the two of you are before believing that you're heading towards another level with him, aight? Bet.

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