Questions About Past Relationships to Ask Your Partner

All 100 questions

The first 4 are on us.

01
What was the 'worst' date you've ever been on before you met me?
02
What is the most 'embarrassing' reason you've ever broken up with someone?
03
What is the longest you've ever gone without talking to a partner during a 'break'?
04
What is the most effort you've ever put into 'stalking' someone online?

05
What is the 'red flag' you usually ignore in people that you definitely saw in me at first?
06
How many 'talking stages' have you had in the last year before we met?
07
If you had to pick one 'toxic' trait from your past self that still pops up, what is it?
08
What is the one thing your parents know about your ex that they don't know about me?
09
What is the most 'toxic' thing an ex ever convinced you was normal?
10
What is the 'weirdest' place you've ever hooked up with someone?
11
What is the most 'scandalous' thing you've ever done in a car?
12
Give me a 1-minute summary of your worst breakup. Don't leave out the messy parts.
13
How many times have you 'circled back' to an ex before meeting me?
14
What is the one thing an ex did that you will 'never' allow in this relationship?
15
What is the one thing you've done in a past relationship that you would never do with me?
16
Which ex of yours do I remind you of the most, and is that a good thing?
17
Have you ever had a 'dream' about an ex since we started dating?
18
Have you ever sent a nude to someone you didn't actually end up dating?
19
Show me your 'Archive' on Instagram. I get to pick one photo for you to un-archive.
20
What is the one thing about my 'past baggage' that actually scares you?
21
Have you ever stayed in a relationship just because the sex was too good to leave?
22
Have you ever compared our relationship to your previous one and felt like something was missing?
23
What is the one thing about your 'baggage' that you're most tired of carrying?
24
Let me look at your 'Recently Deleted' album. If there's an ex in there, you drink.
25
What is the one thing you've 'learned' from your past that makes you trust me less?
26
Do you ever wonder 'what if' about someone from your past?
27
Give me your phone. I'm going to look at your 'Search History' on any app of my choice.
28
Show me your 'DM requests' folder. We are going to look through the 'Hidden' ones.
29
Have you ever hooked up with someone just to get over me during a rough patch?
30
Hand me your phone. I'm going to search a common 'ex name' in your messages and see what comes up.