One to avoid? "How many men have you been with?"
Sometimes it's tough to know what to say — especially for anyone who lacks social skills. In order to make your first few dates smoother, Ask Men has created a list of what not to say to the lady you are getting to know. This will help you from opening up a conversation you thought you were prepared for, but will really just torpedo any chance of having a good time. Here are a few examples of terrible conversation starters, and how to replace them with more friendly questions.
1. "How many men have you been with?"
Just as she should never ask how many women you've been with, you should never ask her how many men she's slept with. The reason you should never ask this question is because you don't want to know. It doesn't matter if the number is high, low or smack dab on the nose of what you’ve deemed "acceptable" — there is nothing to be gained from the knowledge of how many other men she's been with sexually. The only thing it will do is change the way you feel about her. If it's too high, you'll think she just gives it up to any guy, and if it's too low you'll wonder if there is something wrong with her.
Instead Say: "How many long-term relationships have you been in?"
If you must know, or find yourself in a situation where you have to ask, it's better to steer the question away from sex and more towards relationships. If she's been in two to three relationships, and all have been more than a couple years, you can take an educated guess as to the total number of sexual partners. If she's a serial dater, a rough number will pop into your head. If you have to ask, stay away from the word sex, and focus on dating history.
Find the rest of the advice at Ask Men: Things You Should Never Say To A Woman