FIRST DATES FOR SHY PEOPLE
A first date can be absolutely grueling. It’s hard enough deciding what you’re going to wear. Then you get face to face and you have to remain calm and figure out what to talk about to this person you know nothing about. You want to let them know a bit about you without totally spilling your whole life story and you also want to get to know a bit about them... You're shy though and it seems that in these situations you've been a deer in the headlights. You need a toolkit to help you get over the hump of some of that nervousness.
Below are some basic questions to get the ball rolling. Some of these are rather mundane but they could spark up other conversation that can get things in the flow… and of course, any question you ask… be prepared to answer the same about yourself for them...
And remember… these questions are just guidelines… I wouldn’t suggest actually printing them out and insisting on addressing every one of them. Just use them for ideas and see where it goes from there.
Stage 1: The first 10 minutes
These first questions are just starters. Yes, they’re a bit boring and dry but they’re a place to start and give you a little small talk while you’re waiting for the server to take your order.
1. What do you do for work, and how long have you been doing it?
2. Where are you originally from?
3. Do you like living in the mountains? Near the beach? Etc?
4. What did you study in school?
5. What part of town do you live in? Do you live alone? Do you live with anyone?
Stage 2: After the first drink arrives
This next phase should help you get to know them a bit more. Your questions are curious, inquisitive and playful. These should give you an idea of what are some of their likes and dislikes and what kinds of things you have in common in your spare time. The way that they answer can start to give you a clue about their personality.
6. What do you do like to do for fun? When you’re not working…
7. What type of music are you into?
8. Do you like going to concerts?
9. Are you someone who likes to go out or do you prefer to stay in on the weekends?
10. Have you traveled anywhere cool lately/do you have any trips coming up?
11. What’s the most interesting trip you’ve ever taken?
12. When’s your birthday?
Stage 3: Things are starting to get comfortable…
At this point, things are going pretty well and the conversation is flowing pretty well. You seem to get along and you’re excited to learn some deeper things about them. Some of these questions may open conversations that you or your date don’t feel ready to dive into and others will bring up some funny stories. Enjoy the way this loosens you both up and have fun really getting to know eachother.
13. What’s your favorite nationality of food to eat?
14. If you could only eat one thing for the rest of your life, what would it be?
15. Do you like to cook?
16. Do you have any nicknames?
17. Do you have any siblings?
18. What are your family relationships like?
19. What’s your biggest pet peeve?
20. If you could have any super-power, what would it be?
21. What’s on your bucket list?
22. Are you a morning person or a night person?
23. Do you like your job? What do you want to do next?
24. Do you consider yourself career-driven?
25. Do you consider yourself to be a responsible, planning person or a spontaneous, free-spirit?
26. Are you an introvert or extrovert?
27. What’s your social life like? Do you have a big group of friends?
28. What are you most passionate about?
Stage 4: Will there be a Second Date?
Time to seal the deal—Do you two want to hang out with them again? Is there any potential here? If you enjoyed yourself, let them know. These last few minutes are the moments to set the stage for if/when you’ll hang out again. If you like them, think about being a bit more proactive then “I’ll text you sometime…”
29. Can I split the check with you? Okay, can I at least leave the tip?
30. Do you have any fun plans for the rest of the week.
31. Do you have a busy week coming up?
Stage 5: Continue on later into the night
This part should only be used if you really feel good vibes with the person. Otherwise you’re missing your opportunity to make a clean getaway… but… if you really want some more time with them tonight (and this is not just for a booty call) it’s totally appropriate to suggest a next phase.
32. There’s this cool bar I know around here, want to go grab a drink?
33. Want to get coffee/dessert after this somewhere else?
34. My friend’s actually having a party a few blocks away, do you wanna stop by?
35. What are we doing after this?