Brianne Hogan
June 06, 2018 6:00 am
Getty Images

Besties are truly the best. We can share with them our innermost secrets and ask them tons of questions about everything and anything, including dating. Dating is one those intimate subjects that’s reserved for our ride-or-die friends only, which is why it’s so fun and interesting to spill all the tea together on dating and relationships. Considering National Best Friends Day is right around the corner on June 8th, there’s no better time to curl up with your BFF and ask tons of questions about L-O-V-E. Which is why we’ve come up with a list of questions to ask your best friend about dating — some silly, some serious — to further deepen your bond.

You might think you know everything about your best friend, but if you ask her these questions, you’re sure to discover something new. Like maybe her opinion on love at first sight or how she feels about monogamy. Really, who better to counsel about dating than your soul sister?

We asked Shasta Nelson, CEO of GirlFriendCircles.com (a friendship site for women) and author of Frientimacy: How to Deepen Friendships for Lifelong Health and Happiness for her opinion, and these are her top suggestions for questions to ask your BFF about dating.

1. What factors or feelings matter most to you in determining whether you go on a second date with someone or not? How do you decide?

2. Based on who you’ve dated so far, do you think you have a “type?” What have they had in common?

3. If you had to err on one side: Are you someone who tends to get out of relationships too fast, or stay in them too long? Why do you think that is?

4. Based on either your current relationship or a recent one, what are some of the specific things your partner/ex does/did that leave you feeling most loved? (i.e. gifts, affirmations, acts of kindness)

5. In some ways we’ve all been conditioned to believe that a “perfect” mate is strong, attractive, educated, confident, makes money, etc., even though we know those things aren’t correlated to happy and healthy relationships. So, how hard or easy is it for you to be open-minded to dating outside of that narrow “ideal”?

6. When you’ve been in a relationship with someone, how has that tended to affect your friendships?

7. What have you often wished a friend would do, or not do, when you’re dating someone new? In other words, what role do you wish they’d take or what do you wish they most understood?

8. Is there anything you want me to hold you accountable to when you’re dating? Anything you want me to remind you about yourself, or any question you want me to ask you about the person you’re dating?

9. Do you have a pattern that many of your dating relationships tend to follow? How has that cycle served you, and how do you wish it could change?

10. What kind of a person have you often wished I would date? What qualities or values do you think bring out the best in me?

11. When I’m caught up in dating someone new, what is the number one thing I can do to make sure you always feel seen and loved by me? What matters most?

These questions are soul-searching and soulful, and will lead to a night filled with laughter, wisdom, maybe tears, and, most importantly, love.

Advertisement