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There are some questions which you just can’t ask on dates. You may not have the intention to offend- you may think you are being considerate, funny or just making conversation- but offend you will if you ask these dynamite questions.
Not only should you religiously avoid these questions on a first date; you should probably avoid them forever. They’re questions which are so rude that you need to be very close before asking them, and even then you might offend.
Some guys think that the way into a woman’s pants is to ask her about her previous experience. But asking her intimate questions isn’t flirty- it’s crossing a boundary. You don’t know what will make her feel uncomfortable. You should avoid interrogating someone that you want to sleep with about what she’s done in bed before.
Your date probably also does not want to know what you’ve been getting up to. You’re also setting yourself up for problems later if things get serious between you. If you end up getting together, she especially will want to know as little detail as possible about your sexual history so she can’t get jealous.
“When was your last relationship?”
You’re both on the dating scene; it’s a reasonable assumption that at least one of you has recently been ejected from a relationship. But you don’t need to ask about it! You don’t want to make her think about her past- it might make her upset, or it might make her realise that you’re nothing in comparison to her previous partners.
“You’re not religious, are you?”
It’s fine to ask her if she’s religious, but don’t pass judgment about it until you know the answer. If you phrase it in a way that puts her beliefs down, she’s going to be embarrassed. More importantly, she’s going to realise straight away that you don’t support her beliefs, which can be a deal-breaker.
“Do you come here often?”
This line is such a cliché. It’s not even okay to say it as a joke. It isn’t that funny, and highlights the awkwardness of dates. She also might not know if you are serious or not, which could lead to even more awkwardness.
You can ask variations of this question, like “have you been here before?” because it’s not as much of a canned line. It’s also much more open-ended and conversational.
“Are you on a diet?”
It can be easy to accidentally ask her if she’s on a diet if it’s a food based date. But if you ask her if she’s on a diet, she will get the idea that you think she should be on one and could easily become offended.
You might think you are being considerate by asking her if she’s on a diet before committing to an unhealthy restaurant. In this case, it is better to ask her if she likes the food at whatever restaurant it is. If she freaks out at how calorie-laden it is, she can just say that it doesn’t appeal to her without ever mentioning the d-word.
Now, here’s an article with some good first date questions.