The Three Questions NEVER to ask her on the first date–From An Upscale Matchmaker

Understandably, you want to ask question when you go on a date with an attractive woman. That’s part of the process of getting to know her. However, there are certain things you can say that will simply push her away from you. It’s very important that you avoid the following if you ever want to see her again.

1. “Am I the kind of guy you like?” 
Even though you may be quite anxious for her to like you it’s best to not ask her to openly “evaluate” you.

Dating is a process, so you can’t expect her to make an instant decision. There is another point to keep in mind. If you already don’t think you’re worth her time that’s what she’ll end up believing too.

People pick up clues about us by looking at our own self-assessment. So if you need her to validate whether she should date you or not, she will just conclude that she’ s better off without you. Such questions only make you look insecure- don’t ask them!

2. “What’s the worst experience you’ve had with a guy?” 
I know it seems crazy but some people actually ask this! The thing is this question puts her in a negative state of mind. In addition she will start associating those bad experiences… with you. You definitely don’t want this to happen.

It’s better for you to concentrate on pleasant topics. It’s usually best not to ask too many questions about past relationships when you’re on your first date with her.

Ask her about her aspirations, things she likes and how she looks at herself. That will give you a lot more insight about what kind of person she is.

3.”What does it take to be your boyfriend?” 
Oh no! This is probably the worst one. It’s an absolute destroyer of any chances to ever be with her.

This question makes you look needy and spineless. Why?

It’s because it suggests that you are going to act in a way you think she is guaranteed to approve of. The reality is that she knows no man can be exactly the way she wants him to be.

The better approach is to be who you are without being scared of offending her. The fact that she doesn’t like something about you doesn’t mean she will stop being attracted to you. Remember, women despise men who constantly try to please them.


Nicole Westwood is an upscale matchmaker who specializes inupscale matchmaking and executive matchmaking. She ownsPerfect 10 Introductions, which is a matchmaker based in Beverly Hills and works with clients in New York, Los Angeles, Mimai, Dallas, London and Paris.


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