It can be helpful to set boundaries for yourself ahead of time so you can enforce them later. For instance, are you ready to have sex with your date, or would you be more comfortable just kissing or making out?

“Do you want kids one day?” “Do you ever want to get married?” “Do you see yourself living in the city long-term?”

“I’m not really looking for anything serious right now. What about you?” “I’d like my next relationship to be a fully committed one. I’m getting tired of the dating game. ” Try to be upfront about what you’re hoping to get out of the relationship, too. [6] X Expert Source Imad JbaraDating Coach Expert Interview. 5 November 2019.

It’s okay to not be 100% sure about the person you’re seeing just yet. If you enjoy their company and you like hanging out with them, it’s worth seeing them again.

Try to avoid anywhere that would prevent you two from talking, like a noisy bar or a movie theater.

You might go for a hike and then grab lunch, or meet up for drinks and then go get dinner.

Hopefully, your date will feel comfortable enough to do the same!

“Where did you grow up?” “Are you close to your parents?” “What made you want to move to Chicago?”

“Where do you see yourself in 5 years?” “What does your ideal relationship look like?” “What’s your main passion outside of work?”