A Male Relationship Coach Shares 7 Questions Women Should Ask Men On The Third Date

Ready to know if he's the one? These questions can give you some real clarity, sis.


Life really is a trip. Today, the reason why I say that is because, the backstory on this particular relationship coach is, he's actually a good friend of mine. We went to college together. He knew my late fiancé. And now, here we are—both coaches in matters of the heart. The funny thing about Jay and myself is that we have always really interesting discussions on coaching/counseling couples because we're both super-opinionated when it comes to what we think is the key to making relationships work and last. That said, if you've read even a few of my relationship articles on this platform, you know that I can't stress enough, just how important it is to hear a man's point of view if you're interested in, well, dating a man.

In walks Jay. As we were recently chatting it up about how couples should communicate in the early dating phases of their relationship, I asked him to share what he thought single marriage-minded women should be comfortable asking a man around the third date. Because, let's be honest, y'all—if you're interested in jumping a broom sooner than later, time is of the essence and no one is interested in spending precious time, effort and energy in a man who isn't in the same book, let alone on the same page. So, if you've got a guy who you're really feeling right now, you got the "first attraction date" and "second chemistry date" out of the way, it's now time to tackle what Jay says is the compatibility portion of the program. And this can—and in many ways should—transpire on date three.

"The purpose of these questions is to really see if you and he are a good fit," Jay explains. "If after you ask these seven questions, you and the guy you're seeing aren't on the same page, you really should take a step back. You need to assess if there is something actually there beyond emotions and hormones because, unfortunately, about 80 percent of couples don't have these conversations early on—and they end up paying for it later." As a marriage life coach, I can certainly vouch for that (check out "The 'Pre-Commitment Interview' Every Dating Couple Should Have").

So, are you ready to read about what your third date conversation should consist of, again, if marriage sooner than later is on your list of short-term goals? Here are seven of them, along with why Jay finds them to be absolutely essential.

1. "Where do you see yourself in five years?"


A man with laser focus is definitely going to be able to envision where he's headed in life. If he is also marriage-minded, while he's sharing his vision for the next several years, at some point, marriage and possibly children are definitely going to come up. You won't have to coax him into mentioning it. It's already on his radar.

2. "What short-term goals are you looking to achieve?"


The reason why this is so important is because it helps you to get a window into his current priorities. As he's discussing his plans and desires, listen to see if he brings up the kind of woman who he would like to share the rest of his life with. If he's interested in making that move within the next couple of years, he'll mention it. It won't just be in passing either.

3. "How do you feel about children?"


Unfortunately, a lot of couples don't discuss this enough on the front end. While it doesn't apply to all men, if the guy you're seeing says that he isn't interested in having kids and he doesn't already have some, it could send a potential red flag that he's not the most responsible person.

When we have children, they are more permanent than relationships in a lot of ways. A man who isn't interested in kids could be letting you know that he's not big on commitment.

4. "What's your relationship like with your parents?"


You need to know how he was raised. It's no secret that generations can repeat the same patterns. You need to know what you're getting yourself into. How has his father impacted his life? What is his relationship like with his mother, to this day? Now that he's an adult, does he have a healthy set of boundaries with his family? Does he see indications of lasting trauma from his childhood that have gone unaddressed? This might seem like a deep question for a third date but if he's comfortable with who he is, and you're willing to answer this question too, he should be pretty forthcoming about it all.

5. "How important is sex to you?"


On a scale of 1-10, ask him how much he values sex in a relationship. First, in a dating situation and then once he's married. While you're dating, it can let you know what his expectations are. And since sex is often seen as being recreational fun when you're single, it's a good idea to get a hold of how he sees marriage once he's a husband. Sex is a way to cultivate a special bond once you're husband and wife. What are his views on that?

6. "How do you prioritize your health?"


Health is important in every facet of your life—mind, body and spirit. You need to know how he views things like eating habits, working out and going to therapy if/when needed. You also need to know if he expects similar things out of the person he is dating on a serious level.

This might seem like a minor thing when you're dating but when you're sharing a life with someone else, it becomes pretty big.

7. "What does faith look like in your life?"


Even though I'm saving this for last, I easily could've mentioned it first. Because I'm a Christ-centered relationship coach, I believe that two people should be equally yoked. Faith is paramount because it's foundational when it comes to understanding someone's values. When values don't align and two people have totally different forms of reference, it's hard to walk together in life. Not to mention raise kids. Know what his faith/religion is. Know if he makes it a top priority. Know how he wants to implement it in his home someday when he's sharing it with other people. It's pretty important to be on the same page or at least have some common ground here.

BONUS: "How do you feel about blended families?"


I got married for the first time in my mid-40s and one of my two daughters [JH2] was living with me. My wife had no children. We had to learn how to create a blended family. The reality is the longer any of us wait to get married, the greater chance that we'll either be a parent and/or date someone who is. You need to know if he's open or not open to coming into a ready-made dynamic. You also need to see if he's being compliant about the thought of a blended family or just…tolerant. If he's embracing the idea, he'll be really direct about it in his words and his body language. He'll make direct eye contact. He won't dodge the topic. If he's merely tolerant, he might say something along the lines of, "Well, if that's a part of the package" or, "If that's what I've got to do then…"

Marriage is challenging enough. You don't want someone who isn't really willing to make a blended situation work if you've got kids.


Yeah, I know. While a part of you might wonder if these questions are "too heavy", as if you are low-key interrogating him, it really is all in the delivery, tone and if you are willing to answer the questions that you're asking. Besides, remember that this is for those of us who are dating with the desire of meeting the one we want to marry—again, sooner than later. The sooner you know if "he" has the same perspective as you, the easier it will be to either move forward with him or to cool things off so that you can keep yourself open for the one who you can go on three dates with, direct these questions towards and it ends up being all good.

I mean, it's not like a man—a married man—didn't just give the green light to take this approach. There's no time like the present to know where you stand, right? You've got Jay's cosign. Do it.

Jay Hurt is a licensed relationship coach with 10 years of experience. He's also a speaker and the author of two books: The 9 Tenets of a Successful Relationship and Before You Jump the Broom. A great way to connect with Jay is to participate in his bi-weekly open Zoom calls, Relationship Convos with a Black Man. For more information, hit him up on all socials (Facebook, Twitter, Instagram) at jayhurtcoaching or email him at jay@jayhurt.net.

Featured image by Shutterstock

You may not know her by Elisabeth Ovesen – writer and host of the love, sex and relationships advice podcast Asking for a Friend. But you definitely know her other alter ego, Karrine Steffans, the New York Times best-selling author who lit up the literary and entertainment world when she released what she called a “tell some” memoir, Confessions of a Video Vixen.

Her 2005 barn-burning book gave an inside look at the seemingly glamorous world of being a video vixen in the ‘90s and early 2000s, and exposed the industry’s culture of abuse, intimidation, and misogyny years before the Me Too Movement hit the mainstream. Her follow-up books, The Vixen Diaries (2007) and The Vixen Manual: How To Find, Seduce And Keep The Man You Want (2009) all topped the New York Times best-seller list. After a long social media break, she's back. xoNecole caught up with Ovesen about the impact of her groundbreaking book, what life is like for her now, and why she was never “before her time”– everyone else was just late to the revolution.

xoNecole: Tell me about your new podcast Asking for a Friend with Elisabeth Ovesen and how that came about.

Elisabeth Ovesen: I have a friend who is over [at Blavity] and he just asked me if I wanted to do something with him. And that's just kinda how it happened. It wasn't like some big master plan. Somebody over there was like, “Hey, we need content. We want to do this podcast. Can you do it?” And I was like, “Sure.” And that's that. That was around the holidays and so we started working on it.

xoNecole: Your life and work seem incredibly different from when you first broke out on the scene. Can you talk a bit about the change in your career and how your life is now?

EO: Not that different. I mean my life is very different, of course, but my work isn't really that different. My life is different, of course, because I'm 43. My career started when I was in my 20s, so we're looking at almost 20 years since the beginning of my career. So, naturally life has changed a lot since then.

I don’t think my career has changed a whole lot – not as far as my writing is concerned, and my stream of consciousness with my writing, and my concerns and the subject matter hasn’t changed much. I've always written about interpersonal relationships, sexual shame, male ego fragility, respectability politics – things like that. I always put myself in the center of that to make those points, which I think were greatly missed when I first started writing. I think that society has changed quite a bit. People are more aware. People tell me a lot that I have always been “before my time.” I was writing about things before other people were talking about that; I was concerned about things before my generation seemed to be concerned about things. I wasn't “before my time.” I think it just seems that way to people who are late to the revolution, you know what I mean?

I retired from publishing in 2015, which was always the plan to do 10 years and retire. I was retired from my pen name and just from the business in general in 2015, I could focus on my business, my education and other things, my family. I came back to writing in 2020 over at Medium. The same friend that got me into the podcast, actually as the vice president of content over at Medium and was like, “Hey, we need some content.” I guess I’m his go-to content creator.

xoNecole: Can you expound on why you went back to your birth name versus your stage name?

EO: No, it was nothing to expound upon. I mean, writers have pen names. That’s like asking Diddy, why did he go by Sean? I didn't go back. I've always used that. Nobody was paying attention. I've never not been myself. Karrine Steffans wrote a certain kind of book for a certain kind of audience. She was invented for the urban audience, particularly. She was never meant to live more than 10 years. I have other pen names as well. I write under several names. So, the other ones are just nobody's business right now. Different pen names write different things. And Elisabeth isn’t my real name either. So you'll never know who I really am and you’ll never know what my real name is, because part of being a writer is, for me at least, keeping some sort of anonymity. Anything I do in entertainment is going to amass quite a bit because who I am as a person in my private life isn't the same a lot of times as who I am publicly.

xoNecole: I want to go back to when you published Confessions of a Video Vixen. We are now in this time where people are reevaluating how the media mistreated women in the spotlight in the 2000s, namely women like Britney Spears. So I’d be interested to hear how you feel about that period of your life and how you were treated by the media?

EO: What I said earlier. I think that much of society has evolved quite a bit. When you look back at that time, it was actually shocking how old-fashioned the thinking still was. How women were still treated and how they're still treated now. I mean, it hasn't changed completely. I think that especially for the audience, I think it was shocking for them to see a woman – a woman of color – not be sexually ashamed.

I hate being like other people. I don't want to do what anyone else is doing. I can't conform. I will not conform. I think in 2005 when Confessions was published, that attitude, especially about sex, was very upsetting. Number one, it was upsetting to the men, especially within urban and hip-hop culture, which is built on misogyny and thrives off of it to this day. And the women who protect these men, I think, you know, addressing a demographic that is rooted in trauma that is rooted in sexual shame, trauma, slavery of all kinds, including slavery of the mind – I think it triggered a lot of people to see a Black woman be free in this way.

I think it said a lot about the people who were upset by it. And then there were some in “crossover media,” a lot of white folks were upset too, not gonna lie. But to see it from Black women – Tyra Banks was really upset [when she interviewed me about Confessions in 2005]. Oprah wasn't mad [when she interviewed me]. As long as Oprah wasn’t mad, I was good. I didn't care what anybody else had to say. Oprah was amazing. So, watching Black women defend men, and Black women who had a platform, defend the sexual blackmailing of men: “If you don't do this with me, you won't get this job”; “If you don't do this in my trailer, you're going to have to leave the set”– these are things that I dealt with.

I just happened to be the kind of woman who, because I was a single mother raising my child all by myself and never got any help at all – which I still don't. Like, I'm 24 in college – not a cheap college either – one of the best colleges in the country, and I'm still taking care of him all by myself as a 21-year-old, 20-year-old, young, single mother with no family and no support – I wasn’t about to say no to something that could help me feed my son for a month or two or three.

xoNecole: We are in this post-Me Too climate where women in Hollywood have come forward to talk about the powerful men who have abused them. In the music industry in particular, it seems nearly impossible for any substantive change or movement to take place within music. It's only now after three decades of allegations that R. Kelly has finally been convicted and other men like Russell Simmons continue to roam free despite the multiple allegations against him. Why do you think it's hard for the music industry to face its reckoning?

EO: That's not the music industry, that's urban music. That’s just Black folks who make music and nobody cares about that. That's the thing; nobody cares...Nobody cares. It's not the music industry. It's just an "urban" thing. And when I say "urban," I say that in quotations. Literally, it’s a Black thing, where nobody gives a shit what Black people do to Black people. And Russell didn't go on unchecked, he just had enough money to keep it quiet. But you know, anytime you're dealing with Black women being disrespected, especially by Black men, nobody gives a shit.

And Black people don't police themselves so it doesn't matter. Why should anybody care? And Black women don't care. They'll buy an R. Kelly album right now. They’ll stream that shit right now. They don’t care. So, nobody cares. Nobody cares. And if you're not going to police yourself, then nobody's ever going to care.

xoNecole: Do you have any regrets about anything you wrote or perhaps something you may have omitted?

EO: Absolutely not. No. There's nothing that I wish I would've gone back and said to myself, no. I don’t think at 20-something years old, I'm supposed to understand every little thing. I don't think the 20-something-year-old woman is supposed to understand the world and know exactly what she's doing. I think that one of my biggest regrets, which isn't my regret, but a regret, is that I didn't have better parents. Because a 20-something only knows what she knows based on what she’s seen and what she’s been taught and what she’s told. I had shitty parents and a horrible family. Just terrible. These people had no business having children. None of them. And a lot of our families are like that. And we may pass down those familial curses.

*This interview has been edited and condensed

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