Going On 100 Dates to Find Love

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100 dates

My podcast guest, Holly Martyn, went on 100 dates to find love after her second divorce. She’s the author of Would it Kill You to Put on Some Lipstick: 1 Year and 100 Dates. She’s a writer, storyteller, frequent flyer and former Wall Street executive. Born in Toronto and raised near Vancouver, Canada, Holly is a graduate of Columbia University and holds a master of fine arts degree in creative writing from Queens University of Charlotte in North Carolina. She divides her time between homes in Connecticut and California with her daughter and dog. In this episode, Holly shares her story of going on 100 dates to find love!

Listen to EP 400: 100 Dates to Find Love

What inspired you to write the book?

I was going through a divorce, and I thought I should channel all the angst into my writing. I picked up a magazine in a spa, and I read a story about a widow who crossed paths with Joan Rivers, who told her, “Would it kill you to put on some lipstick? Go on 100 dates and meet someone!” It inspired me to stop feeling sorry for myself and go on dates to meet men. The book became about me reflecting about the choices I made in life. How can i do better in the next part of my life.

One of my biggest areas of growth and learning was when I met a man in a bar who asked if I was divorced. I said, “Yes”, and he asked how many times. When I said twice, he yelled, “Two-time loser”. This was what I had been afraid of all the years I had been married—what would others say about me? It was freeing to hear this jackass insulting me. I realized the only thing that matters is how I think of myself.

How did you go about trying to get 100 dates?

I did a few things. I went online and signed up for some apps. I also told myself whenever my daughter was visiting with her dad, I would eat at a restaurant alone and strike up conversations. And then, I told friends and family I was interested in being set up. 

It worked! I transformed my life quickly. I had lost some friends in the divorce, and this process brought wonderful men AND women into my life. 

Can you share some dating tips you learned along the way? 

  • Use the apps. I like Hinge and Bumble.
  • Put the word out to family and friends that you want to be set up. What’s one hour out of your life?
  • The other funny thing I learned is I used to wear pretty cocktail rings, but some men thought I was married. The minute I stopped wearing rings, I got asked out more. 
  • If you’re worried about what to wear, set aside five date outfits that you feel good in no matter what. 
  • Prioritize your love life. It’s not magical thinking. Choose to find love.
  • Once you get the dates, be smart about screening up front. Keep eyes and ears open. Listen carefully and believe people the first time. There are red flags you have to look for. I started to respect them. If a man tells you he doesn’t know or want a relationship, believe him.

What have you learned as someone who often goes out to eat by yourself?

At first I felt uncomfortable. But, I was getting out of the house. So, I put down my phone, and I chatted with the bartender and people to my right and left. People spoke to me. People crave conversations. Everyone can teach you something, even if you don’t date them. As women we’ve been conditioned by society that women who go out alone are ‘looking for something’. We need to rethink that. It’s not sleazy. 

Watch the video of EP 400: Holly Martyn – Going on 100 Dates to Find Love

Connect with Holly https://www.hollymartyn.com/

Please subscribe/rate and review the podcast here.

If you’re feeling stuck in dating and relationships and would like to find love this year, sign up for a complimentary 1/2 hour breakthrough session with Sandy https://lastfirstdate.com/breakthrough

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Watch the book trailer – it’s fun!


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