Consider popping a few of these questions on your next first date and see where they lead the conversation. What do they wish they could have done differently, if anything? You don’t have to rapid fire interrogate someone, of course, but it can lead to a conversation about their past that’s meaningful but still light. This isn’t meant to prompt a confession of your date’s failures. What about you, what do you wish you were better at? This question will let your date show their vulnerable side, and admit to something they’re not entirely comfortable with, particularly if you chip in first to show solidarity.
If nothing else, you’re bound to get some interesting answers. Maybe it’s about being with their pet dog in the backyard or the smell of their grandmother’s house. The best way to approach it is as a light-hearted thing by offering an example of your own. ” Or, “True fact, I didn’t learn how to tie my shoes until I was in high school.” It’s a way of letting your guard down and laughing at yourself, a very attractive quality, and an invitation for your date to do the same. What things would you save if your apartment were on fire?
Especially when we get stock in an awkward moment of silence, we desperately scramble for something interesting to say.
I for sure know the feeling of running out of interesting conversation topics, though it feels like a “prier life” a century ago I was the king of awkward interaction until one day where I decided to do something about it, today I have used the last 10 years to study the art of conversation (and other social skills).
Questions that avoid the conversational boxes that turn a fun opportunity into a dull exchange.
As a general rule, never do this, in any way, ever, til death.
The reason is because you’ll come off like every other horn dog guy.
Too many guys ask girls questions that are either too boring (“Come here often? ”), too silly (“If you could be a flavor of Kool-Aid, what flavor would you be?
”) or too much like a job interview (“What do you want to be doing in five years? What you need aren’t just questions, but good questions.