Look, I don’t know about you, but I do not have time to be sitting across the table from somebody’s grown son trying to figure out if he’s emotionally constipated or just slow. 😂 As a solo mom with a schedule tighter than my bra at the end of the day, I need to know quick if we’re even in the same lane.
So no, I’m not here for the surface-level “what’s your favorite color?” convos. My first date questions (or first convo if we meet up online) are intentional, grown, and designed to save me from wasting good lip gloss and bothering my parents.
Here are the 10 questions I always ask and why:
1. “What does a healthy relationship look like to you?”
This one right here? A temperature check and a values check all in one. If his answer sounds like a Drake lyric or he says “I’ve never thought about that”… baby, no. At this big ol’ age, he should know.
2. “What’s your relationship like with your family?”
How he talks about his folks tells you a lot, especially his mama. If he calls her “crazy” or has unresolved issues with her, that might be a red flag. Even if he has daddy issues, that might be something worth diving more into. Cause what you don’t need is for his unresolved trauma to be taken out on you. Yeah… no thanks.
3. “How do you handle conflict?”
I’m not arguing with no grown man who throws tantrums or gives the silent treatment. We grown—use your words big fella! So be sure to really pay attention to what he says—and doesn’t.
4. “What are you working on within yourself right now?”
Healing is sexy. Accountability? Even sexier. If he’s not doing any inner work, don’t let him come disturb your peace. So if his answer is, “Whatchu mean?” Check please!
5. “Do you want kids or see yourself in a blended family?”
As a solo mom, I need to know early if he sees my child as part of the package—or just baggage. Ain’t no in between. As I’ve mentioned before, I prefer men who already have children as I’m not willing to budge on having more children. But just be sure that your desires align with his.
6. “What does consistency look like for you?”
Because effort one day and ghosting the next? Not in this season. If he can’t show up regularly, he doesn’t need access. So if he doesn’t see any issue with not communicating on a daily basis, he may not be the one. This question will probably also need follow up questions just to dig deeper cause some of these men will just tell you what they think you want to hear.
7. “What’s your vision for your life in the next 3-5 years?”
I’m not asking for a five-year PowerPoint, but if he’s just “seeing what happens” in his life, I’m gonna need him to see himself away from me.
8. “How do you recharge after a stressful day?”
This one helps you see how emotionally intelligent he is. Does he know how to soothe himself, or is he gonna turn into a tornado and expect you to clean it up? Or does he turn to certain unhealthy habits that don’t align with your lifestyle?
9. “Who do you go to when life gets hard?”
Men with no tribe worry me. If he doesn’t have even one healthy connection outside of you, he’s probably gonna lean on you for everything. That’s not love, that’s emotional dumping. Also, if he has no connection to a Higher Power, that’s an automatic NO for me and if you’re a believer, it should be for you too.
10. “What’s something you’ve had to unlearn about love?”
Now this one will stop a man in his tracks. And the answer will tell you everything. If his response is overly negative, especially towards women and not self reflective in any way, congrats—you just saved yourself six weeks of wasted texts.
Dating as a solo mom is already a balancing act—I’m not out here dating for sport. I’m dating with intention, with curiosity, and with the understanding that my time, my peace, and my energy are sacred.
So next time you’re on a first date, take the pressure off trying to impress. Ask the real questions. And if the vibe’s off, don’t force it. Your person won’t mind being asked the deep stuff, he’ll be grateful you did.
Your turn: What’s one question YOU always ask on a first date? Drop it below—I’m always adding to my list! 💬👇🏽
Great questions!!