Christian Singles & Dating

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What You Should Never Ask on a First Date

What You Should Never Ask on a First Date

“How much do slaves cost?” 

Ah, autocorrect, thou art a heartless shrew—I was trying to ask how much skates cost! But that single, autocorrected text message (sent right before my first-ever date) was the question that must have cursed the rest of my romantic life. 

Let me show you what I mean…

1. “Hasn’t anyone ever said you look like a childhood actress who hit the party scene too hard and is now trying to make a comeback?”

Fall was in the air. I glanced across the picnic table at my date. 

“So,” I said, breaking the ice, “do you have a favorite movie?” 

Trevor shook his head. “You?” 

“Well, I love The Parent Trap.” 

“You actually remind me of Lindsay Lohan,” he said.

I smiled, flattered. “Because we share a name?” 

“No.” A pause, too long. Then, “Hasn’t anyone ever said you look like a childhood actress who hit the party scene too hard and is now trying to make a comeback?” 

I laughed at his joke.

He didn’t.

There wasn’t a second date.

2. “Do you know God brought us together to be husband and wife?”

The African sun was burning my scalp (something they never tell you about in missionary school). One of my preschool students raced up to me. 

“Teacher, teacher!” she said. “Pastor wants to speak to you.” 

I picked her up and walked over to the strange man on the outside of the playground fence. 

“You are a missionary, no?” the pastor asked.

He cut me off before I could answer.

“Do you know God brought us together to be husband and wife?”

I rolled my eyes. Turns out, my brain wasn’t the only thing getting fried by the blistering heat.

3. “Does it make you insecure that I’m a lot smarter than you?”

“I work in video marketing at a publishing company,” I said.

“Oh,” Robert replied. I waited for something more, but was left hanging.

 So I said, “You’re an engineer, right?”

“Aerospace engineer, actually,” he said. 

“That’s impressive. Was it a lot of schooling?”

He squinted his eyes, just ever so slightly. “I have my PhD. So yes.” He paused, then asked me, “Does it make you insecure that I’m a lot smarter than you?”

“Nah,” I said, mentally crossing his name out of my address book. After all, a truly smart man would never have asked a girl that question, right?

4. “Who was the guy in your Instagram picture from last May?”

It was a scene directly from a romantic comedy. Sleigh bells rang, Christmas lights twinkled, and conversation danced between us. It was the first time we’d ever met, and things were going well! 

Then this happened…

“Can I ask you a serious question?” Kyle said, taking my mittened hands into his. 

“Sure,” I said.

“Who was the guy in your Instagram picture from last May?” 

Stalker alarm bells started sounding in my head. My Instagram is set to private, how did he… nevermind. Kyle and I never made it to Christmas.

(And not that it’s any of your business, but the guy he was talking about was my brother!)

5. “I’m thinking this will be your last first date. How do you feel about that?”

I should’ve known better. The warning signs were all there! Obsessively talking about his brother’s wedding. Begging to watch Say Yes to the Dress. “Jokingly” saying my first name worked well with his last name.

It was official: I’d landed myself a first-date husband. 

“I’m thinking this will be your last first date,” Cooper swooned. “How do you feel about that?”

Not so great, I said to myself. Of course, looking back on the question, I think maybe he was on to something: 

I should probably take a break from first dates…

At least until Saturday. 

35 More Things You Should Never Ask on a First Date…

6. Why do you think all your past relationships have failed?

7. Are you on a diet?

8. Is it cool if my parents come to dinner, too?

9. Wow—your mom is hot. Do you think you’ll look like her in 25 years?

10. Is your roommate seeing anyone?

11. Do you think you talk a lot?

12. How many kids should we have?

13. Is that your real hair?

14. What’s one thing I could say to you right now that would scare you aware from a second date?

15. My mom wants to know if you believe in predestination.

16. Don’t you think your laugh is kind of loud and obnoxious?

17. I mean… What’s your pants size? Like an 11?

18. Is it okay if I wear my rollerblades into the restaurant? 

19. You seem so normal. What’s really the matter with you?

20. Where do you want to meet? I’ll have my mom drop me off.

21. Does it bother you if a person talks to himself… a lot?

22. Why do you make such funny faces? 

23. What’s the cheapest wedding ring I could buy you?

24. Where do you see this relationship going?

25. Do you usually eat this much food?

26. Do you think none of your relationships have lasted because you have a fear of commitment? 

27. Do you ever wish your lips weren’t so big?

28. You look really tired. Are you sick?

29. So… you’re not underage anymore? 

30. If you could be any flavor of bagel, what would it be?

31. How much do you weigh? 

32. Why are you so pale?

33. If this relationship continues, can I touch your behind in public?

34. Have you ever seen a person die?

35. What’s your biggest insecurity? 

36. I still live at home. Is it okay if I kiss my mom on the mouth every night?

37. You brought your wallet, right?

38. Want to just order off the dollar menu?

39. It’s okay if I ask you to completely stop talking to other guys, right?

40. How’s your biological clock doing?

So… Now What?

So what’s next for me and my “cursed” romances? 

Well, first I just have to remember Romans 8:28 (KJV) even applies to my dating life: “And we know that all things work together for good to them that love God.” God will use these moments to help me prepare for that really good date awaiting me in my future: My wedding day! 

Second, next time any of us goes on a date, I think we all might want to keep in mind the wise advice found in Ephesians 4:29 (NIV): “Let no unwholesome word proceed from your mouth, but only such a word as is good for edification according to the need of the moment, so that it will give grace to those who hear.”


Publication date: August 29, 2016