Asking For a Date in 3 Steps

Asking For a Date in 3 Steps

How to ask a man or woman on a date in 3 steps

When I was in high school, I had a friend who knew Kurt Vonnegut’s daughter, Lily. I met Lily once or twice back in the late ’90s.

Fast forward to 2012. I was sitting in a hotel room in Miami, thinking about things to write to you about. The New York Times Weddings/Celebrations secion is always a good place to look for inspiration. And there it was, Lily Vonnegut marries Brian Michalski.

My first questions were: Who is this guy? And how did they meet? The article said:  The couple met in July 2010, when Ms. Vonnegut, who had sprained an ankle, went to the physical therapy clinic where Mr. Michalski worked…On her last day of therapy, she asked him if he would like to hang out sometime.


There are lots of ways to ask someone out on a date.  When I was in high school, and beepers outnumbered cell phones, I figured out how beep “Will you go out with me?”  That wasn’t the brave way to do it.

Asking out your potential partner by email or text isn’t brave, either.

Looking back at what I did, I wonder why I was so timid asking Cara on a date when I already knew she liked me.  After all, she gave me her phone number, so what was I afraid of?I am going to teach you how to be braver than I was, and ask for a date then-and-there, and you’ll do it in three steps…


I believe in taking risks, but not stupid risks.  You only ask out a potential partner whom you believe is interested in you.  How do you know if your potential partner is interested in you?

That’s what the entire last post was about!  (If you didn’t get it in your inbox, then you aren’t getting the Free Dating Guide.  Grab it here.)


A lot of people ask their potential partners on dates at an inopportune point in the conversation. What do I mean by that?

Well, imagine that you are talking with someone you find attractive.  You have a great conversation. Then, the conversation starts to slow down.  You feel like you have to salvage it and land a date before the conversation dies completely.  So you ask, “Do you want to go out sometime?

Even though that works sometimes, notice that you’re asking out your potential partner when the conversation is on the decline.  You have a much better shot as scoring a date when you ask as the conversation has gathered momentum!  

To gather the conversation momentum you’ll need, for Step 2, you’ll need to find out specific activities your potential partner enjoys doing.  Once you know what he or she enjoys doing, you’re going to use that information to your advantage in Step 3.


I was taking the subway home with my softball teammate (a female).  Also on the subway with us was a substitute player on the team.  They started chatting as I got off the train.

The day after the game, she called me for help figuring out whether the substitute player asked her out on a date.  Yes, you read that correctly: my teammate didn’t know whether the substitute player asked her out on a date, and she wanted me to clarify that for her.

Here’s the scenario…

After I got off the subway, my teammate and the substitute player were talking about Jay-Z.  In their conversation about Jay-Z, he mentioned that he was going to the Jay-Z concert that weekend. He mentioned that he had extra ticket.  Then the substitute player asked my teammate for her phone number so that they could arrange a place to meet before the concert.

Boom!  He asked her out and she didn’t even know it.  He did that by making The Ask part of the conversation.

That is what Step 3 is all about.  By weaving The Ask into conversation, you can arrange a date without the stress of asking, “Will you go out with me?

Some examples of ways you can wave The Ask into conversation:

Person 1:  I have always wanted to try Restaurant XYZ.

Person 2:  Great!  I do, too.  How does your schedule look for Friday?

Boom!  You nailed The Ask!

Or try this one:

Person 1:  My favorite comedian is Lewis Black.

Person 2:  I love him.  Let’s try to get tickets for his show next week.

You nailed The Ask again!

How else would you do The Ask?  Drop your ideas into the Comments, below.


My wife, Lisa, and I have two cats, Poppyseed and Sesame.  (We all them “our bagels.”)  As I write this to you, Poppyseed is lying next to me and squeaking.  Why does she squeak?  Because she can’t meow.  But I totally know what her squeaks mean….

She is squeaking to remind you to share this email with your friends and post it on your social networks by clicking these:  Facebook Twitter Google+ LinkedIn StumbleUpon.


  • Whenever possible, ask your potential partner on a date in person rather than electronically
  • Step 1:  Determine whether your potential partner likes you
  • Step 2:  Figure out what activities your potential partner would enjoy
  • Step 3:  Weave The Ask into conversation
  • Share your best Asks in the Comments, below
Jeremy Hamburgh
Jeremy Hamburgh
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  1. Tony Langdon says:

    Love it! Great advice, though it can be a bit trickier for neurodiverse people, but not impossible. On the flip side, if you’re on the receiving end of such an invitation, and you like the person making the invite, GO FOR IT Accept it then and there. :)

    This is getting into the sort of thing I’ve experienced, where I often say “I don’t date as such”, meaning that any dates I’ve had haven’t felt like dates, they were simply shared outings that developed on their own (actually, I never had any intention beyond “friends” until after meeting :) ).

    For those on the autism spectrum and/or with anxiety issues, the less you make a date seem like a “date”, the higher the probability it may work out, because you’ve reduced the pressure on yourself to “make it work”. However, you have to be flexible enough to go where the date (or “non date that turns into a date”) leads, to be able to accept unexpected opportunities.

  2. The story about Lily Vonnegut, this is exactly what I done when I met Zena at group therapy and plucked up the courage to ask her out after several sessions but was prevented by Angela the occupational therapist despite Angela saying to me a few weeks earlier, we’ll have to get you a girlfriend. I asked her out using my own initiative but the forces that be acted against me as usually. This caused me more psychological damage, not so much as if she had rejected me but because the silly rules prevented me from going on a date which would have done me the world of good. That was 15 yrs ago and the closest I’ve been to going on a date. All what’s left of me now is the bitter remains of a lonely asperger male with no hope for the future.

    • Jeremy Hamburgh says:


      I am sorry that your efforts at asking Zena out were blocked. That is hugely frustrating. As much as it can hurt the ego to be rejected, the only way to win at dating (and at life) is to keep trying and “putting yourself out there.” As I always say, you can lose a thousand times at dating, but you only need to win once to be champion.


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