15 questions about
embarrassing stories
Pick one and start there. You don't have to go in order.
- 1
"What's your most embarrassing memory that you can laugh at now?"
- 2
"What's something embarrassing you did as a teenager you've never fully recovered from?"
- 3
"What's the most embarrassing thing that's happened to you in public?"
- 4
"What's something mortifying you did on a date — not with me?"
- 5
"What's an embarrassing habit you had that you've never admitted to?"
- 6
"What's a social situation that still makes you cringe to think about?"
- 7
"What's an embarrassing fashion choice from your past?"
- 8
"What's the most awkward thing you've ever said to someone important?"
- 9
"What's something embarrassing about you that I already know?"
- 10
"What's something embarrassing about you that I don't know?"
- 11
"What's the most ridiculous thing you've ever cried at?"
- 12
"What's an embarrassing moment from our relationship you can laugh at now?"
- 13
"What's something you said that you immediately wished you hadn't?"
- 14
"What's the most embarrassing song you have on your phone?"
- 15
"What's something about yourself you'd find hard to admit to most people?"
How to use these
conversation starters
Over dinner
Pick one question at the start of the meal. Let the conversation lead where it wants.
On a long drive
No eye contact makes some questions easier. Road trips are perfect for depth.
Before sleep
One question each before the lights go out. This becomes a ritual you'll both love.
On a walk
Walking side by side reduces pressure. The movement helps the conversation flow.
Sunday morning
Slow morning, no agenda. Phones down. One question over coffee.
In the app
Log your answers in Relationship App: Love Story. Look back on them together.
Keep the conversation
going every day.
Daily prompts, mood check-ins, love notes, and a shared memory of every conversation you have together.