Episode #173 Ask Them Out

How many of us have waited so long to ask someone out that by the time we finally muster the courage, they are already dating someone else? This week, Dr. Michael Brown and single dad Ricky May consider how to take dating seriously without taking it so seriously.

Show Notes

I know guys who will hold back because they are like, "She’s out of my league." But I’m like, "Bro, step up! Get on another level.”
Ricky May

Five Problems

  • If we wait to move until we feel confident, we will find ourselves stagnant.
  • We tend to enter the dating scene with the goal of getting something in the short term rather than giving something in the long term.
  • A romantic partner is never the cure for our insecurity or identity issues.
  • There is nothing sexy about caution and overthinking.
  • The talking stage was created as a concession to our fear.

Five Principles

  • The dating pool is much larger than we think.
  • We are more likely to identify shared interests and values with someone we meet while engaging in hobbies than with someone we meet at a bar.
  • Asking someone out is more effective when we have a specific date and plan in mind.
  • There is something magnetic about us when we enter each space more interested in others than interesting to others.
  • Dating requires intentionality and thoughtfulness, but it doesn’t require certainty.

Three Practices

  • Reframe rejection not as a failure but as proof that you have successfully taken a risk.
  • When asking someone out, consider the polite and casual way that you would want to be asked out.
  • When on a first date, focus on having a good time getting to know the other person without any expectation or pressure for what the future holds.