Reflect After the Third Date

Jasbina asks Neely Steinberg – Author of the book ‘Skin in the Game: Unleashing Your Inner Entrepreneur to Find Love’: After getting past the third date, you suggest that daters reflect on four different questions. The first one is, “Do I feel good about myself when I’m around him?” Tell us about that.


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Neely Steinberg

To give the listeners context, the chapters are broken out. I already mentioned my “date, learn, repeat” model of entrepreneurial dating. 

Chapter five is all about dating and taking action.

What we’re talking about now is in chapter six, which is the “learn” part of that model.

You are learning and reflecting on the experiences that you’re having so that you can act in smarter and more empowered ways.

Acting in smarter, more empowered ways is the “repeat” chapter — but it’s actually more about building as opposed to repeating without learning anything. You build on what you’re learning from all the action you’re taking out there in the dating world.


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In chapter 6, I encourage the reader to ask themselves 4 questions after their third date and beyond with someone.

Questions to Ask After the Third Date

  1. Do I feel good about myself when I’m around him?
  2. Do I feel good about the bond and connection we’re forming?
  3. Do we value similar things in life?
  4. How is our relationship growing?

Elaborating further:

1) The first one is, “Do I feel good about myself when I’m around him?”

I think it’s really important to be with someone who appreciates you and allows you to be who you are and feel good about that. It’s someone who brings out your best attributes.

If you find yourself feeling emotionally off kilter and unsure of yourself, that’s something to reflect on and think about.

2) The second question is, “Do I feel good about the bond and connection we’re forming?”

Do you feel like there is a real connection growing? Is there a bond? Do you feel safe and secure in the connection that you’re forming? That dovetails off the first question.

If you find that this connection is unstable, he pops up every now and again, it’s time to consider whether this is really the person that is going to be in that vision that you create in chapter two.

3) The third question is, “Do we value similar things in life?”

You’ll start to discover as you start dating someone what they value. What are the things that he values in life? You don’t need to have 100% of the same values.

If you have certain fundamental values, he doesn’t ask you to change those values nor do you ask him to change some of his more fundamental values.

Maybe there are some other values that you can work with a little bit.

Religion, for instance, wasn’t really important to me. I’m Jewish but I wasn’t religious growing up. Dave is Catholic. That was a value that wasn’t really all that important to me. I was willing to compromise on that.

Other values in my life were really important to me. I wouldn’t want to be with someone who asked me to compromise those fundamental values.

4) The final question that I encourage women and men to ask themselves after the third date and future dates is, “How is our relationship growing?”

I like to put it in terms of an entrepreneurial venture. Is it:

  1. Slow growth
  2. Hyper growth or
  3. Steady growth?

How is your dating and love venture growing?

1) Slow growth is if you’ve been dating for a few months but things feel really stagnant. It’s progressing really slowly. There is no real effort on the part of your suitor to move things forward, even though you’ve expressed interest in doing so.

That means that you’re ultimately settling for crumbs. You should really want the whole cake.


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2) Then there is hyper growth.

I don’t know if you’ve worked with people who get involved in these relationships. After a week, they’re already talking marriage and moving in together.

Sometimes, in that type of scenario, you really get caught up in that frenzied pace without pausing to think about your feelings. Is this really the right person?

3) Then there is steady growth.

You’ve been dating for about two to three months. This isn’t an exact science, of course. Things feel like they’re growing naturally, organically and at a healthy pace. You’re taking time to get to know each other and figure out your feelings for one another. There is no pressure from either person. It feels like a steady, upward trajectory.

I have seen relationships in low growth and hyper growth work out. I would encourage women to predominantly seek out steady growth in a budding relationship.


Do You?:

After your third date, do you begin reflecting on your growing relationship? Is the third date too soon to analyze a relationship?


The above is an excerpt from Jasbina’s interview with Neely Steinberg.

The entire interview transcript is at: Neely Steinberg Interview – Unleashing Your Inner Entrepreneur to Find Love

Listen to the entire interview on: Intersections Match Talk Radio – Jasbina’s Lifestyle Show

Listen to the entire interview on Blog Talk Radio: Unleashing Your Inner Entrepreneur to Find Love – Neely Steinberg

Listen to the entire interview on iTunes