“Your questions are creating an awkward situation for her”
It doesn’t matter if it’s your first date or your fifth date, if you’re going out with someone to get to know them then there are some questions that you need to avoid entirely. After you’ve gotten to know a person and actually start a relationship with them then you can talk about whatever you want. But making that first impression is key when you actually want to get to that stage. Some of these questions might seem innocent, but it’s the underlying meaning that really can screw things up.
“How Do I Look?”
Again, this might seem really innocent but it’s actually setting up a very awkward first meeting. She can’t say “Oh you look terrible” because that’s just rude. She only has one option, and that’s to say you look good. The date would already be off to a rough start. Even beyond that you’re coming off as the type of guy who needs to be praised about his looks. Talk about shallow.
“So What Happened With Your Ex?”
A lot of people think that this is the type of question you should ask to get a gauge of how she acts in a relationship. Plus you get an idea of what you can avoid to end any future relationship that might come around. But really all you’re doing is bringing up bad memories. Even beyond that you’re getting off to a very difficult start.
“What’s Your Five Year Plan?”
“I was here for a date not a job interview!”
Getting to know someone by asking what they want to do in the future isn’t the worst idea. What’s your dream job? If you could travel anywhere next year where would you go? Those are appropriate. But asking someone’s five year plan is putting them on the spot and making them come up with some pretty personal information. They might not even think that it’s all that bad, but most people don’t actually have a plan. The lack of plan can also make them feel like they’re disappointing or not on par with other people.
“Why Are You Single?”
Seriously? This question is just entirely rude. That’s like asking someone “Why are you ugly?” Alright, it’s not exactly the same, but it has the same sort of sting. Most likely if she’s been single for a while she’s had many sleepless nights with pints of ice cream asking herself the same thing. It’s a sad thing; to be single for a while (if it’s not by choice). Bringing that up will make her feel uncomfortable and taken aback. There’s no way to leave a good impression with this question.
“How Much Money Do You Make?”
There’s a reason that you’re not allowed to discuss wages at work. It’s because it can cause jealousy and envy them. The same thing goes for your date. If she makes less than you then she’ll feel bad and vice versa. Even more than that, you may come off as a gold digger who wants a sugar mama.