First Date Questions

First Date Questions That Work & The Truth About Dating In Your 30’s


Season 2 of Very Cavallari starts March 3 and just like last season, you guys will get a major peak inside my dating life. Based off these pics from filming days, I think it’s pretty obvious that I agree, dating can be tough and confusing.

Dating can be confusing

With Valentine’s Day on the horizon this week, dating and relationships are all people seem to focus on. I wish I had some sage advice to offer on how to make the dating process easier or find your soul mate, but truthfully the best I can give is the hope that I do believe love is out there and also just the comfort that you are NOT alone in your struggles to find it. Since we are all just figuring it out as we go, I figured we could use a little help. I did some research and found some awesome articles on first date do’s and don’ts , dating in your 30’s (like me) and how to try and enjoy dating and the journey.
Here are my favorites, click the article to learn more:

9 Harsh Truths About Dating in Your Late 30s

This one lays it out pretty bluntly.

Dating In Your 30s Just Feels Different – Here’s How To Find What You’re Looking For

When I read this I felt like my BFF was giving me a pep talk and kick in the pants all at the same time.

First Date Conversation Tips That Won’t Make You Seem Weird

These conversation tips are spot on.

40 First Date Questions That Always Work

This article breaks a date down into phases, providing questions for each phase and also gives some transitional conversation tips. I felt the info for Phase 2 and beyond to be beneficial.

13 Great First Date Questions Backed by Science

These questions won’t make you or your date feel like you’re on an interview.


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