Questions to Ask About Life & Funny Questions
To Get To Know Your Boyfriend


Have FUN! Asking great questions always opens up interesting conversation. Make sure that you are a keen listener and are not rushing them. Sometimes males take a little longer to open up. If you can get them telling stories that relate back to their answers you will have endless good times. So enjoy yourself and ask away.

History Questions and Conversation
Starters for Your Boyfriend


When was the first time that you had beer?


Who were your role models when you were younger?

As a child, what did you want to be when you grew up?

When and with whom was your first kiss?

What is your earliest memory?

What did you enjoy about school?

Name 1 thing you miss about being a kid.

Who was your enemy or the bully when you were young?


What was your favorite musical group when you were in Junior High?

What was your favorite childhood injury?

When you first met me, what was the first thing that attracted you to me?

What extremely difficult life situation have you overcome and how did you do it?

What is the most embarrassing thing ever to happen to you?

Was there ever a time when you were frightened for your life?

Worst roommate you have ever had

What was the last national park you visited?

What is your worst dating experience?

Which is the best summer vacation you’ve ever had?

What about your best ski vacation?

Have you ever hitchhiked?

What was your Halloween Costume for Halloween last year?

Which is the most funniest prank played on you or played by you?

What is the craziest thing you have ever done?

Name someting you did as a child that your parents don’t know about.

Have you ever been so drunk that you had to be carried out?


Have you ever stayed at a luxury hotel room....what was your hotel room like?

Do you own any dirty magazines?

Have you ever had phone sex?

How many sexual partners have you had?

What do you remember about your high school prom?

Have you ever been mentioned in a newspaper?

What is the hardest drug you have ever done?

What friend has influenced your life and how did they do that?

Tell me about your first road trip in your first car


Boyfriends Questions Categories
Facts | Family | History | Preferences | Philosophies | Future | Dirty