First Date Questions: 100 That Aren’t Boring

All 100 questions

The first 4 are on us.

01
Coffee, tea, or the drink you actually order when you are trying to seem interesting?
02
Sweet, salty, or the kind of person who dips fries in a milkshake?
03
The song you would put on to instantly improve any car ride.
04
Dogs, cats, or some chaotic third option I am about to hear about?

05
Texts, calls, or the person who replies three days later with a paragraph?
06
Summer person or winter person, and what makes you so sure?
07
The weirdest food combination you genuinely enjoy and will defend.
08
Your karaoke song — the one you secretly know every word to.
09
If your week had a soundtrack, what genre is currently playing?
10
The last thing that made you laugh so hard you had to stop what you were doing.
11
What kind of kid were you — shy, chaotic, teacher's favorite, or full menace?
12
What were you actually thinking the first time we talked?
13
The most 'main character' moment you have ever had in real life.
14
The dream you have been quietly carrying that you do not talk about much.
15
Were you nervous before tonight? Be honest about it.
16
Something you have changed your mind about completely as you have gotten older.
17
The personality trait you are most drawn to in other people.
18
How do you know when you are starting to really like someone?
19
The version of your future that genuinely excites you when you let yourself imagine it.
20
What is something you are insecure about that you are slowly making peace with?
21
A fear you have about dating that you do not usually admit on a first date.
22
The kind of relationship you are quietly hoping to find.
23
The thing about yourself you are most nervous someone new will misunderstand.
24
What is something you want to be different in your next relationship than your last?
25
The thing you are secretly hoping happens by the end of tonight.
26
What is the first thing about me you found genuinely attractive?
27
What is the most attracted you have felt to someone just from a conversation?
28
Be honest — have you thought about kissing me tonight?
29
If tonight did not have to end, what would you want to happen next?
30
What part of me have you been trying not to stare at all night?