The other day, I started thinking about my worst first date ever. The unpleasantness of the date had everything to do with my overeagerness, which was evident in the questions I started asking about five minutes after we ordered our food.
Even though I barely knew my date, I asked about her plans for marriage, childbearing and career. And let me tell you, it was awkward, awkward, awkward. Unfortunately, due to my inexperience with dating at the time, I didn’t even realize I was making her uncomfortable.
Based on that first date, I decided to make a list of some of the most awkward first-date questions you can ask. The day after I started drafting my list, my friend Liz posed this question on Facebook: “What’s your favorite first date question?”
It inspired one of my favorite Facebook comment strings ever. And after conferring with the Boundless team, we added a few more to the list. Here’s the complete list of awkward and inappropriate first-date questions you can use if you only want to go on first dates for the rest of your life:
1. “Are you thinking about marriage in the background a little bit — even though this is just sort of our first date?”
2. “Would you like to be my accountability partner?”
3. “You gonna eat those fries?”
4. “Is that your natural color?”
5. “What about me attracts you to me?”
6. “Oh, so you own your condo? How much did you pay for it?”
7. “Why are you single?”
8. “What was your name again?”
9. “Thanks for getting dinner with me tonight. Do you mind watching my cat for me this weekend?”
10. “Have you ever struggled with your weight?”
11. “I’m guessing you’re a size 8. Am I right? I think size 4 is ideal.”
12. “What race are you exactly?”
13. “Would you be open to watching a seven-part series on Calvinism and telling me what you think?”
And last but not least, my friend Jay offered this classy response: “Why would I ask a question? That just takes time away from me talking about myself.”
Something tells me our readers can add more questions to this list. Don’t hold back — let’s hear them.
Copyright 2016 Joshua Rogers. All rights reserved.
