6 Cringe worthy Questions Women Dating Should Stop Asking: Dating these days is already like finding the perfect plantain—ripe, sweet, and without disappointment. So, why are we making it harder for ourselves with these awkward questions? We’re older, wiser, and frankly, too grown for certain nonsense.Sometimes, it’s us asking the cringeworthy questions that make men retreat faster than Wi-Fi on a bad day. Let’s be real: some of us are out here scaring off perfectly decent men with cringeworthy interrogations that belong on Married at First Sight altars. Let’s not be that person I beg. For the men you can find there here:
Ladies, we need to do better. Here are 6 cringeworthy questions women dating should stop asking. These need to be banished from your dating repertoire:
1. “Where do you see this going?”
Context is key. Sis, it’s date three, not a strategy meeting with HR. Asking this too early puts unnecessary pressure on both of you. We’re all for intentional dating, but ease into it. Yes, we’re not here for vibes and vibes alone, but asking this too early makes you sound like you’ve got a PowerPoint presentation titled Our Future Life Together. Relax. Date first, interrogate later. Timing is everything.
2. “Why did your last relationship end?”
Do you really want to hear about his messy breakup while you’re sipping your mojito? Unless you’re training to be his therapist, don’t make this your business on date one. Sure, you want to know if his ex filed a restraining order, but maybe let that information come out organically. If you ask this question on a date, be prepared to be asked the same—and how many of us want to go there straight away?
Men will either dodge the question or hit you with a tragic monologue about their ex. Neither is ideal. Wait until he volunteers the story.
3. “How much do you earn?”
In the Black British dating world, this question has the same energy as asking for his National Insurance number. Yes, financial stability matters, but interrogating his salary gives off “I’ve already planned our joint mortgage” vibes. Pay attention to how he lives and what he prioritises. The answers are always in the details.
4. “Do you date Black women?”
Listen, the racial dating discourse is real, especially here in the UK, but asking this can sometimes come across as defensive rather than empowering. If he’s on a date with you—a beautiful Black woman—it’s clear he’s interested. Let’s not start the night by making him feel like he’s taking a GCSE test on race relations. Asking this can make you sound like you’ve been burned one too many times.
5. “When are you going to settle down?”
This one might feel justified if you’ve been dating someone for a while, but it’s still a landmine. Some people hear “settle down” and think compromise, stability, or mortgages. Others hear ball and chain. Instead, ask about their values, goals, or what they’re looking for long term. You’ll get the answer without without scaring him into ghosting.
6. “Do you see me as wife material?”
Pause. Are you auditioning to be someone’s life partner, or are you a grown woman who knows her worth? This question not only gives him all the power but also tells him you’re looking for validation. Babe, you’re the prize—act like it. If he doesn’t see your greatness, that’s his L, not yours.
Final Thoughts
So there are your 6 Cringe worthy Questions Women Dating Should Stop Asking. Dating is hard enough without turning it into a Q&A session. We’ve all asked some variation of these questions before, but dating is about connection, not cross-examination.Instead of grilling him, focus on creating a vibe that makes both of you want to keep exploring. Stay playful, stay curious, and keep the awkward questions for your group chat.
What’s the cringiest question you’ve ever asked—or been asked—on a date? Let’s share and cringe together.
© Chelsea Black ® 2025
