11 Questions To Ask Your Girlfriend About Her Past


These might be the toughest kinds of questions to ask your girlfriend because they are deeply personal.

We all have baggage. And while you may think her baggage won’t affect you, or that you can leave the past in the past, the unfortunate truth is that unresolved issues from the past do ruin relationships — many relationships!

To get to really know your girlfriend, and particularly what she brings to the relationship, you will have to know where she came from, what she’s been through, and how even-keeled she is. These questions will help you do that.

1. What was your most serious relationship? How long did it last? Why did it end? What did you like or dislike about him?

First of all, try not to get jealous when she starts waxing poetic about her ex-boyfriends, OK? After all, you’ve probably also been around the dating block.

The purpose of this question is to learn about her dedication when in relationships and ability to accept responsibility for her mistakes, as well as how she handles conflict.

If you notice similarities between your partner’s descriptions of her past relationships and your relationship with her, it could indicate a pattern that may need to be addressed.

2. What was the best gift you’ve ever given to someone? What is the best gift you have ever received?

We all love receiving gifts, but not enough people like giving them.

These interesting questions to ask your girlfriend should give you some insight into how considerate and thoughtful she is of people, and what she values in people, things and experiences.

It’s also an excellent opportunity for her to brag about herself.

3. Have you ever cheated on someone before? What happened?

This can be a very touchy question to ask your girlfriend, so tread lightly.

That being said, cheating in relationships is so common that it’s a question worth asking. If she comes clean to you, try to find out why she did it, if she felt bad doing it, and whether or not she’s ever been cheated on.

Try to gauge how accountable, responsible, dedicated, and fair she was to the person she cheated on. After all, there is some truth to the old adage “once a cheater always a cheater.” If her reasons for cheating seem unreasonable, there is a good chance she will cheat on you.


4. How much time did you usually spend with ex-boyfriends? Did you think it was too much time, or not enough time? What did you usually do with your ex-boyfriends?

Once again, don’t be that guy who gets jealous over her girlfriends ex-boyfriends.

Some guys like their girlfriend to be around them all the time, while others prefer some distance. On the same note, some girls like spending as much time with their boyfriend as possible, while others don’t.

This series of questions to ask your girlfriend about her past should give you an idea of how much space you should be giving her.

5. Have you ever been in a relationship when you weren’t in love?

Dude, have you been dating a gold digger all this time? Is she only with you so that she can gain material benefits?

All jokes aside, if your relationship is just starting off and you still don’t know her that well, a question like this can give you a peek into her motives.

But don’t be quick to cast judgment If she answers yes. Ask some follow up questions to truly understand why she entered into the relationship.

6. How many relationships have you been in?

It can be very difficult to know if a woman is telling the truth about how many partners she’s had, so why bother asking, right? Why should you even care?

I’ll tell you why you should care: Studies show that a woman’s likelihood of infidelity is positively correlated with the number of people she’s slept with. So the more partners she’s had, the more likely she will cheat.

I don’t want to sound cynical, but that’s just the way things are. She may or may not be honest with you about her partner counts, but don’t let that stop you from doing what little you can to get a ballpark estimate… without being creepy about it, that is.

7. When did you lose your virginity? How did you lose your virginity?

You need to be very, very careful with this question. It isn’t one you can just ask willy nilly.

You might think it’s all fun and games, but you never know the can of worms it will open or even if you’re prepared for the answer. What if it turns out that she lost her virginity to a guy who raped her?

These types of questions to ask your girlfriend should be reserved for when the two of you are very close and open with each other.

8. Do you have any regrets from your past relationships?

People like to believe they live a life without regrets, but how can anyone really learn to do things differently if they’ve never felt bad about their decisions?

The truth is, many of us have regrets, and relationships are one area where even the smartest among us are bound to screw up.

The lessons, if any, see learned from her past relationship mistakes will transfer over to your relationship, so it’s worth knowing.

9. What was your best day ever, and why?

When someone tells you about the best day of their life, you are essentially getting a  blueprint for who they are as a person.

Carefully listen to her answer to find out if the underscoring emotional experience of that day is something you vibe and connect with.

10. What was it like growing up in your family? Are you close with your siblings? What sort of rules did you have in your house growing up?

These open-ended questions to ask your girlfriend can help you learn about her family values and possibly her personal values without targeting specific individuals.

Knowing about her life growing up can give you a whole new perspective on who she is, especially when considering that many of our formative experiences shape our relationships.

11. When you were little, what did you want to be when you grow up? And do you still want it?

She was probably asked this a lot while she was growing up. Has her answer changed now that she’s older?

This is one of the most considerate questions to ask your girlfriend. It gives you an opportunity to find out what she wants so that you can help her achieve it

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