First dates can be very awkward. You both know that it may be the only shot you have to impress someone, and that you could be finding your soulmate, or wasting your time. When you are trying to learn more about another person and wondering if you could see yourself spending time with them, it can feel like you are tiptoeing through a minefield.
To get the best of your date, mix your open-ended questions. Start simple to see how easily they open up, and then progress into more complicated, personal questions as the time goes on. Open ended questions always make you seem a little smarter too because they make you look like a conversationalist. Make sure you lose the list. Sure, you have some very serious questions that you want answered, but you can’t live by the list or you will seem like you are not actively listening to his answers.
If you are super focused on making sure that you tick off every question on your list, then you won’t be focused on opportunities to enjoy yourself. Do not, I repeat, do not memorize the list. If you do this, it will sound like you are giving a questionnaire speech as opposed to actually trying to get to know him. He will be bored by the, undoubtedly, monotone sound of your voice and you recite your list of questions.
Once you have mastered those few critical points, there are about forty questions that can really get the conversational ball rolling, and allow you to figure out everything that you can about your date without seeming like you are working for the FBI and trying to build a case about him. Remember to actually pay attention his answers as this is where you learn if there is a possibility of a future or not.
Make sure you are also paying attention to your feelings about his answers because this is who he is, and if you aren’t okay with it on your first date, you will never be okay with it. If you don’t want to seem like you are drilling him for information, then follow the previous suggestions and try out a few of these questions.
1. Do you like it here? (This could mean the restaurant, or just in the town).
2. What is your favorite drink?
3. How is your food?
4. Have you come to this place before? If so, how often?
5. What was your day like?
6. What kind of work do you do? Or where do you work?
7. What is your favorite kind of music and is it current music, or oldies?
8. What is your favorite food and how often do you eat it?
9. What restaurant is your favorite?
10. Do you have a favorite genre of movies? Hulu, Netflix, cable, Amazon, or Kodi?
11. What is your after-work routine? How do you unwind from work?
12. How do you enjoy yourself when you’re not at work? What do you spend your weekend doing?
13. Where do/did you go to school?
14. Where is your favorite vacation location? How many times have you been there?
15. What is your idea of a fun time?
16. Cats or dogs?
17. If you had the power, what would you change about the world and why?
18. Are men or women the better sex? (Don’t ask this one if you don’t want to know the answer because it could be awkward).
19. Are you closer to one parent than another and has it always been that way?
20. What are your biggest turn-offs in a woman?
21. Are you a casual or formal kind of guy when you are out and about?
22. Do you like chick flicks and what was the last one you saw?
23. Do you always so charming/always look this good?
24. Books, movies, or games? (If he says anything besides books, you might as well give him the boot right then. Okay, that’s a little biased, but still…)
25. Who, in your life, do you admire the most and why?
26. Do you like for things to be spontaneous or routine? Does it matter if it’s your spontaneity or someone’s around you?
27. Who is your confidante that you trust advice from?
28. What childhood memory always makes you smile?
29. If you could leave today to travel the world, what would be your first five destinations?
30. What is your current passion in life?
31. Are you and your family members all close?
32. What do you hate the most to see, or experience, on a first date?
33. Are you a night person, or a dreaded morning person? (Yes, I may have added the dreaded part myself so, no, you don’t have to actually use it.)
If things are going smoothly and he is interested in the conversation, then try some of these next:
34. Where are you the most ticklish?
35. Who was your first crush and how old were you?
36. What are your regular guys nights out like?
37. How would you define the word “relationship?”
38. How long did your last relationship go on and why did it end?
39. How did you feel about this date before you got here today?
40. And how do you feel about it now?
With this plethora of conversation starters, you should have no trouble getting your first date out of the way and leave with a better understanding of who he is deeper down. This is also the perfect time to re-evaluate his answers. If there was anything that threw up red flags for you, then maybe you should consider not having a second date. If you appreciated all of his answers and how he represented himself, then you won’t feel super uncomfortable when you meet the next time.
Remember that you are not obligated to stick around for the whole date. If any of his answers make you want to start running for the hills, then take off girl! There is no point in wasting time sitting around talking to someone that makes your skin crawl. Also, if you ever feel unsafe, don’t walk out alone. Have the waiter, bartenders, security personnel, or just about anyone else escort you to your car because your safety is much more important that trying to look as if you aren’t afraid.
In fact, I highly recommend that you check with restaurants about safe words or orders before you meet that date anywhere. A lot of places nowadays have specific “orders” that alert them to a problem and they will have security come and get you, or call the police. Agreeing to meet that date instead of having him pick you up is a lot safe because he won’t know where you live if things go badly, you won’t have to rely on him for a ride home, and you will feel more confident knowing that you can leave at any time. Always worry about your own safety, because no one else is.
That being said, be sure to try and relax unless you get warning flares from him. Enjoy your night out and maybe, just maybe, that night out will turn into something that you never saw coming. It always happens when you finally stop looking for love anyway, so just kick back, enjoy your life how it is, and take pleasure in the small things. Besides, true happens comes from you, not your dating life.
Don’t believe me? Just go take a weekend to yourself to do one thing that you absolutely love and you will never doubt me again. Celebrate that your life is awesome without a man and the one you are looking for will come waltzing right up to you. Mine did.