"Asking him ‘do you find me attractive, pretty, or interesting,' or anything that screams ‘I'm insecure and I need validation' will scare him away fast. While this is not a question per se, our experts had a bit of advice beyond the initial conversation starters.
Of course he thinks you're great, he did ask you out on a date! You may get comfortable with him and feel like you can share anything over the course of that first date, but Rushford advises, leave your baggage at the door."Everyone has issues, but try not to lead with what a hot mess you are right out of the starting gate.
If they say, "Well, you're hot or you have nice boobs," that might be true and it would be rude if they said they didn't find you attractive, but you want to know that they're going to go deeper than your physical qualities.
Even if you think he could be The One, "you still need to dangle the carrot," says lifestyle expert Samantha Goldberg. "Men like to hunt so don't be a dead deer."According to celebrity dating and relationship coach David Wygant, if you're fantasizing about happily ever after and the pitter patter of little feet, keep it to yourself—for now.
And if they don't respond at all, people might say, "I don't know, it's too deep of a question." You have to ask yourself, "Do you want to be with somebody who would be that quick to shut down?
Or do you want to be with someone who has a little more room to push themselves and go someplace different? I usually suggest this for a slightly older crowd, and this is a question that you have to pull off with a lot of confidence.
Remember, this person doesn't know you and you want to make sure you're sharing much more of the best parts of you than the bumps we all inevitably have."Try to focus on the positives in your life, and not rant about what annoys you—your horrible day, your awful co-workers, or your evil boss.
"This doesn't make you cuter or more compelling," Rushford says.