Ask Wendy

What’s the Right Pace for Dating a New Person?

Friday, March 2, 2018
woman with coffee
Hey Wendy,

I met a guy at a Meetup who asked for my number and, on our first date, brought a list of really fun questions that helped break the ice. Come to find out, when I mentioned some specific ones to my girlfriend, she told me they're the famous 36 questions that lead to love. These questions start innocently enough and become increasingly intense and probing until you're baring your tender little soul, and you have no idea how you got here! The frog has been boiled!

We've been on a medium-length first date and a lengthy second date, and had two lengthy phone convos and still haven't finished all the questions. We always end up going off on tangents and talking about a million other things.

Even though these questions are new to me, and I've never gotten close to someone in quite this way, it seems like I have been burned before, getting too intimate, too early. And even though I would never have picked him, and I had low expectations of our first date, I like this guy. He makes me feel safe and special, and he turns me on. This feeling, too, is familiar to me. Some people advise going slowly while getting to know someone. That's never really worked for me. I tend to develop intense feelings quite swiftly, and if I stay too long in the getting-to-know-you phase before forging ahead into romantic possibility, one of us inevitably Friend Zones the other, and then it's game over, and it all feels like a waste of time.

So, my question is: do you have any thoughts about this? Should I be more cautious? (The very question makes me shudder, as it feels so inauthentic to me.) Should I be this open, vulnerable, and forthcoming this early?

Anna P., Austin, TX

Hey Anna,

Ok, so first off, thanks for providing the readers and me with this inspired list we’ve all heard so damn much about! And I read it to see just exactly how hot that water got for little froggie.

Verdict: I love, love, love these questions! I also love any guy who brings them to a date. It’s a tell about him; he’s interested in knowing you and willing to go deep.

But don’t let my opinion sway your own gut instincts or your process.

See, it turns out that everyone has (or will have) an opinion on your love life. They’ll want to chime in on how it’s going, how you’re conducting yourself, how your dates are showing up, what method, trick, rule or process you’re employing with each date, etc. Because people know, unequivocally, how to date right. They read books, they listen to podcasts, they’re sure of the rules and the best of the best of the best practices, they even know the one TRUE way to get courting done right. Except they’re wrong – because they aren’t you.

Society at large says there’s a right pace for dating a new person and a right way to get to know someone, and that’s taking it slow. Get to know them as a friend first. Your own history tells you that’s the wrong approach for you unless you dig living in the Friend Zone.

Whether you dive in headfirst or tiptoe in from the shallow end, you still end up in the pool. I say continue to use your own good judgment, and trust that your love life has ultimately always worked out the way it was supposed to. The person who’s best for you will like your style and appreciate your approach.

And p.s. Question #6. If you were able to live to the age of 90 and retain either the mind or body of a 30-year-old for the last 60 years of your life, which would you want? – Seriously? Is this a real question? Ha! Now I can’t stop thinking of how much fun I’d have at 90 with that 30-year-old body! I’d wreck that thing! I’d be taken out of this world at 90 while swinging from a chandelier.

Now go enjoy your life.

Do you have a dating, sex or relationship question for Wendy? Send it to