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10 Questions To Ask Your Guy About His Past

Dying to know your lover's secrets? Then spark up this conversation.

It's definitely not the type of light and airy chat you want to strike up on your first starry-eyed date. Let's be honest: Dredging up the past and owning all things that went right and wrong can be about as pleasant as having a root canal.

But precisely because spilling the beans requires such a high level of comfort and trust, a Q&A session (topic: all things past) with your guy can bring the two of you closer in your relationship. And everything from the way he responds to your dig for details to the answers he gives will provide you with clues to help you determine if this love's built to last.

Make the get-to-really-know time fun by asking a mix of questions that conjures memories both good, downright hilarious and, well, maybe not so good. Just be ready to openly discuss your past, too. After all, this isn't an interrogation. Here's a list to get you started.

1. What were you like as a child?

2. What's your happiest memory of growing up?

3. What's the biggest lie you ever told—did you get busted?

4. How many sexual partners have you had?

5. What's the riskiest thing you've done in life? Sexually?

6. Why did you and your last partner split?

7. What disappointed you about your last girlfriend and led you to want to break up?

8. Are you still friends?

9. Who are your best friends in life? Why?

10. What's the most unusual place you've had sex?

Now we want to hear from you! Tell us: What questions did we miss—that you're glad you asked your guy? Plus, what was his reaction? And which of his responses surprised you most?

Can you relate?

Discussion

LordCAG Single built like a rock
Posted October 18, 2009

I think these questions are great. I would add:

1. If you were stuck on a deserted island who would you want with you and why?
an engineer
2. What is the one virtue and one vice you cannot live without, and why?
mike n' ikes
3. What is the extent that you would take it if your most important relationship were in trouble?
turn the world into an abattoir
4. Do you have any regrets, and if so, what are they?
to many the most inportent was not kicking the s**t out of this guy(fellow employee) who threatend me because I didn't wont to get fired then three weeks later I get fired the day after my birth day. but I had to work on my birthday that pissed me off.

Read more: http://www.yourtango.com/200912977/top-10-qs-ask-your-guy-about-past?lid...

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LordCAG Single built like a rock
Posted October 18, 2009

1. What were you like as a child?
shitty.
2. What's your happiest memory of growing up?
none.
3. What's the biggest lie you ever told—did you get busted?
I loved my country.
4. How many sexual partners have you had?
0
5. What's the riskiest thing you've done in life? Sexually?
nothing.
6. Why did you and your last partner split?
never.
7. What disappointed you about your last girlfriend and led you to want to break up?
whore.
8. Are you still friends?
no
9. Who are your best friends in life? Why?
my friend Josh R. known him a long time, plus he's reliable 65% of the time
10. What's the most unusual place you've had sex?
really?

Read more: http://www.yourtango.com/200912977/top-10-qs-ask-your-guy-about-past?lid...

Read more: http://www.yourtango.com/200912977/top-10-qs-ask-your-guy-about-past?lid...

Score: 0
Chrissys16 Taken
Posted September 5, 2009

I would NEVER ask my boyfriend how many women he's been with, particularly because if he asked me, I would lie like a rug (not because I don't love him but because they were all totally irrelevant to our relationship. Plus, with my number, there's no way I could come out of that conversation looking good. Hint: my number is somewhere between pre-marital Jessica Simpson and Jenna Jameson, and that's all I'm gonna say. Likewise, I wouldn't expect him to tell me the truth (nor even WANT to know...it would either disgust me or make me feel guilty).

I'd definitely never want him to know the craziest place I've had sex, mostly because, although it was eight Halloweens ago, I had sex bent over the rail of a glass balcony of an apartment...that is just ONE block away from his place! Somehow I don't think it would be a great relationship strengthener for him to have to drive by that building every day and, each time, have a daily mental picture of me dressed as Alice In Wonderland getting railed on the balcony by some other dude.

Score: 0
dynamike74 Single Witty, adventurous manly man
Posted April 17, 2009

Why do you care how many partners he's had?

What if he turns the tables on you? When you answer honestly, he either thinks you're a liar and a slut or a he thinks you're telling the truth and a slut. It's only asking for trouble.

I say, leave the past in the past and move on. That question is something a high school kid would ask.

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lwarrell Starting Over
Posted February 27, 2009

How about - how heavy is your baggage and how do you carry it? In a backpack, a Louis Vuitton tote, a couple of Glad garbage bags?

Score: 1
Posted February 26, 2009

Have you been engaged or married? Unfortunately my last boyfriend did not divulge this because he thought for some reason that I knew from his longtime friend who is my cousin who just re-connected with him. My cousin had lost touch with him during the years he was engaged since those were the years between high school and age 30! He should have told me himself even if he thought I would have known!

Score: 0
Lyz Married Community Manager
Posted February 25, 2009

the only question you should ask is
1. Did your mom do EVERYTHING for you? And do you expect that from me?

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sheila_79 Complicated
Posted March 9, 2009

thats a good question! i agree with you

Score: 0
Melanie36 Married 5 years happily married
Posted February 24, 2009

I love the hot dog question!

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Alex Complicated No nonsense about love!
Posted February 24, 2009

When have you felt the most proud?
When have you felt the most ashamed?

And, as Jillian from the Bachelor asked: What do you put on your hot dog? She's clever.

Score: 0
Melanie36 Married 5 years happily married
Posted February 24, 2009

I think these questions are great. I would add:

1. If you were stuck on a deserted island who would you want with you and why?

2. What is the one virtue and one vice you cannot live without, and why?

3. What is the extent that you would take it if your most important relationship were in trouble?

4. Do you have any regrets, and if so, what are they?

And the only thing I think is critically important is timing. Ask too soon and he's out the door. Women have to remember that time is on a different continuum for men than it is for women. So when you want to ask, take a deep breath and wait a beat to make sure he's really ready for it! Too much emotional intimacy too fast and he's a goner and so are you.

Score: 0

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