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15 Funny (but not really) Questions to Ask Someone You are Dating

By Winnie Caldwell

Do you find yourself still requiring approval from your parents when it comes to dating? Do you feel at times, they wish they could interview guys before you are smitten? Being a twenty- five year old, single, African American young lady, my parents are protective of me. Though, my BFF’s parents are protective as well. I recently met a guy online who really has caught my interest and I told my BFF about him. While she was excited, she made a point to tell me to check my email. She never contacts me outside of texting/calling, so I was pretty perplexed. I checked my email, and saw I received one from her with the subject line stating, “Thank you for your interest in our daughter.”

Literally LOL, I texted her asking what this nonsense was. She encouraged me to read it thoroughly and ask this new guy all of these questions! These are the questions that get to the nitty gritty and I couldn’t help but share with you!  Below you can find a bit of the questions that I  asked in this very in-depth, humorous, dating interview.

  1. Full Name: You have to know who you are REALLY dating! No ‘Catfish’ this way!
  2. Nickname: Does he/she have a street name or another alias?
  3. Age: Don’t assume you know a person’s age by their looks, because the statement is true for African Americans; Black don’t crack honey!
  4. Height: If this is important for you, you may want to ask. This is very helpful for online dating.
  5. Occupation: Share your career goals and dreams! You’d be amazed what you can find out.
  6. Credit Score: Would you rather find out while dating or after marriage some unfortunate credit history? Surprisingly, people don’t mind sharing this info!
  7. Has a restraining order ever been filed against you? This will prevent you from waiting for red flags down the road.
  8. Have you ever been married? This can open up for an interesting discussion!
  9. Are you currently taking any medications? I think he/she would appreciate you asking, rather than rummaging through their medicine cabinet.
  10. How many “psycho” ex-girlfriends/boyfriends do you have? You may see who the real ‘psycho’ is.
  11. When was the last time you had sexual intercourse? __a few hours ago __a few days ago ___a few months ago __ a few years ago
  12. Can you provide documentation that you are free of any STDs? “Don’t be sorry, be careful!”
  13. How much time do you spend looking in the mirror per day? Selfies count!
  14. Are you a believer? __God ___other
  15. Describe your perfect first date.

Sharing this vision will open up more things you both have in common!

As uncomfortable as some of these questions may seem, keep in mind to have a sense of humor. Have fun with it. I was very nervous and worried when I asked some of these questions. Honestly, I have never thought to ask so many necessary questions when dating before. Sometimes, we as single people are guilty of just living in the moment, and finding things out as time progresses. I then reminded myself of my motto; Hang up your problems and move on to better! Therefore, you cannot go into different relationships the same way, and expect a different outcome! So get your interview voice ready and dig into these great ice breakers!

BMWK, would you feel comfortable asking these questions?

Winnie Caldwell is a Faith Based Blogger, Freelance Writer and Online Publisher of TheWireHangerByWinnie.com. Winnie uses testimonies from trials & tribulations to inspire others. She inspires readers to leave any negativity behind and move forward into pursuing their dream career, ultimate relationship and more. To experience this bright spirit everyone loves, visit thewirehangerbywinnie.com where the motto is “Hang Up Your Problems & Move On To Better.”

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