Fun, Employed, and Moisturized. Now What?

Hey Fam,

Back when I was dating, I asked all the typical first-date questions. What do you do? What do you like to do? Do you have kids?

And if I'm telling the whole truth, I was also quietly running a second evaluation: did this man have some swag? Could he dress? Could he talk? Did he walk into the room like he belonged there? Was there a little seasoning on that situation?

None of those questions were wrong. Shared interests matter. Attraction matters. But here's what I eventually had to admit:

I was screening for an enjoyable date, not a dependable husband.

Maybe you've done it too. You leave saying the date was amazing. What made it amazing? You like the same music, you both love to travel, you laughed all night, he has a great job, and girl, he smelled good.

Wonderful. We have confirmed that he is fun, employed, and moisturized. 🙃

But what else did you learn? How does he handle frustration? Does he have an active relationship with God, or does he just know how to say he's a Christian? Does his life even have room for a relationship? And the one we forget while we're busy wondering if he likes us: Do I like what I'm learning about him?

Now, the fix is not swinging to the other extreme and showing up with 17 questions and three dealbreaker lists like an assistant principal running an investigation. Where do you see yourself in 5 years? Ma'am, he came for tacos.

So what's the middle? It starts with taking some pressure off: you are not deciding whether to marry him. You're deciding whether you have a wise reason to know him better. That's it. No violins, no slow-motion walk through the restaurant. Just enough information to choose the next step.

And to gather that information, you don't need more prepared questions. You need better follow-up questions. A checklist says, "I need to get through my list." Curiosity says, "I want to understand the person in front of me." Scripture backs that posture up: be quick to listen and slow to speak (James 1:19), and know people by their fruit (Matthew 7:16).

With that posture in place, here are a few conversation doors to open naturally:

• "How was your day?" Listen for how he handles frustration. My eyebrow goes up when every story has a villain and somehow he's never it.
• "What does a typical week look like for you?" His calendar may tell you more than his dating profile. Is there room for a relationship, or are you supposed to fit in the seven minutes between Bible study and baggage claim?
• "What are you looking forward to with this relationship?" Then believe what he says, and don't add subtitles he never said.
• "Do you have a relationship with God?" Yes is the beginning, not the evidence. Follow up with: "What does that look like on a Monday?"
• "What does a healthy marriage look like to you?" Listen for what he plans to give, not just what he expects to receive.
• "What kind of life would you like to build?" You don't need identical dreams, but your dreams can't require opposite lives.

Of course, asking good questions is only half of it. The other half happens after the date, once the chemistry is no longer sitting across from you smelling good.

Your homework: for your first 4 dates with a man, take a few quiet minutes at home (not in the restaurant bathroom, Sis) and answer four questions:

1. What did he say?
2. What did I observe?
3. How did I show up?
4. Based on what I know today, do I have a wise reason to accept another date?

After date 4, read all four entries together. One date gives you an impression. Several start to show consistency. And remember, he's still putting his best foot forward. If his best foot is already late, vague, and inconsistent, please don't wait around to meet the other foot.

👉 Listen to Episode 4 now

Because none of this is about making dating heavier. It's about making your decisions clearer. You're allowed to laugh too loud, order dessert, and appreciate a man with a little swag. Just stop confusing a good time with good character. 💛

Hit reply and tell me: which of these questions are you trying on your next date? I read every one.

Date with purpose, and build the marriage God is calling you to.

XO, Lessa

P.S. Know a Sista who already has her first-date questions organized by category and level of urgency? Forward her this with love. We admire the preparation. We're just asking her to let the man finish chewing.

Stay connected, fam:

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