When you start dating a new woman, you want to know her. Getting to know someone involves a heavy amount of conversation and a lot of questions asked so you can learn about each aspect of her personality that you want to know about. There will probably be a few questions that you’re absolutely certain you want to ask her, and for a good reason. The only problem is that with some of these questions, she’ll jump on the defensive immediately and demand to know why you want to know. Many women can be a little touchy about questions regarding their previous sexual partners or why her last relationship ended. In fact, it seems that until things get really serious, she might not even want to talk about her past at all.

Sexual Partners?

“How many people have you been with?” is one of the most important questions to ask any woman you start dating or just hooking up with. If you’re going to start seeing her seriously, she needs to be willing to disclose sexual history when you ask. Most women will, but not without a fight. She’ll get defensive immediately if the topic almost comes up in conversation. The question is hard to phrase, so it may be taken the wrong way and she’ll start thinking you’re insulting her and insinuating she sleeps with everyone and most women will (understandably) become upset about that. Although the question might make her defensive, it’s a good one to ask so you shouldn’t skip on it just for the sake of avoiding conflict.

The Last Relationship

“So, how did your last relationship end?” is another one she won’t answer without a little bit of careful encouragement. When you ask her why her last relationship didn’t work out, it might be a touchy subject. Maybe it ended because the guy cheated on her and she isn’t alright with that, so she won’t want to talk about how she was hurt. Or maybe, they just weren’t sexually compatible because of a particular quirk of hers, so she won’t want to discuss that right off the bat. She might not even want to discuss it further down the road, either. Try phrasing it not so abrasively if you want to get the information out of her. Try mentioning why your last relationship went south and see if that will inspire her to talk.

The Superficial Questions

“How much do you weigh?” is a loaded question and we shouldn’t have to tell you twice that asking this is a terrible idea. She will get mad and if you ask the question out of the blue and sound like a shallow jerk, she’s likely to walk out on your date. Even if she’s fit and beautiful, getting asked about her weight might still be a sore spot. Additionally, asking about her natural hair color, her shoe size, and other appearance-related traits that you might think are alright to may make her jump on the defensive. You never know when something will be an insecurity or sore spot for her, so be careful.