Lessons learned from more than 100 first dates

Jami Goldfarb Shapiro
4 min readMay 2, 2020

Back in November 2017, I created the Facebook Group “50 First Dates”. I invited my Facebook community to join me and I gave myself the following rule — I would not allow myself to “quit” or “give up” dating until I met at least 50 men. ( I didn’t want to meet 50 men. I wanted to meet “the one” and stop counting)

Leading up to this time, I learned as much as I could about dating. I listened to podcasts, read articles, took online webinars and had many conversations with other “daters”.

I read a great book, “Calling in the One”. The author ended up marrying a man she never would have considered dating. If you are really open to meeting someone, you have to let go of your preconceived notions about who you’ll date or not date. For me, saying “yes” when I would have previously said “no” allowed me many experiences I never would have had.

Before the challenge, I waited for men to engage me in conversation and ask me out. As a result of a dating webinar I listened to, I learned a woman does not exist to a man until he’s met her IRL (In Real Life).

Another great book, “If the Buddha Dated”, said you need to show up authentically. If you attract someone wearing a “mask”, eventually the truth is going to come out. This also means communicating honestly about what you want/need in a relationship.

I learned A LOT more out in the field and decided to share it…or you can be like my kids and learn the hard way. Go ahead…touch the stove top and see if it burns ;)

  1. KNOW your love languages. If you are with a partner who does not pay attention or make some sort of effort to “love” you the way you receive love, he (or she) is pretty much telling you ali you need to know.
  2. In the words of Maya Angelou, “When people tell you who they are, believe them.” If you date a man who tells you he sort of disappeared in his last relationships, don’t be surprised when he disappears in yours.
  3. Almost all of us have baggage, especially those of us who are divorced. I have a theory that if we had our shit together, we probably would have been able to work through the problems in our marriage. (Of course not in all cases.) My grandma used the expression “they only change faces”. If you don’t work out your issues, you WILL continue repeating your patterns.
  4. My grandma also used the expression “Too hot not to cool down”. It takes a good three months to really know who a person is. Those love drugs are for real!! If I had a dollar for every time I went on a first date with someone (before this challenge) and said “this is the one”, I’d have at least a $20 bill.
  5. If you are looking for a relationship with someone who will make time for you, pay attention to how long it takes them to schedule the first date. It shouldn’t have been a surprise to me that a man I dated for nearly seven months, didn’t really want a partner when it took him two weeks to even meet me for coffee. Just about all of us (at least those of us with teen age children who don’t travel all the time) can find a half an hour somewhere in their schedule and if they can’t, read the first sentence again.
  6. To thine own self be true. Know who you are and what fundamental qualities and values are important to you. DO NOT COMPROMISE if it’s truly part of your core being.
  7. You attract where you are at. If you wouldn’t date you, what makes you think you’d attract someone else who’d want to? Don’t get me wrong, I had lots of fun with some very hot, EFFed up men when I myself was EFFed up. When I look back on who I was with at the time, it truly is an accurate reflection of who I was at that moment.
  8. Pay attention to the profile. (More on this later.). People will put effort into things that matter to them. If someone puts one picture and little to no description on a profile, you might consider how serious they actually are about meeting someone.
  9. You can’t meet the right person with the wrong one by your side. It’s tempting to stay with someone because they are good looking, fun or have “potential”. Don’t date anyone expecting them to change and do not date potential. Ask yourself “if this person or relationship were to stay exactly as it is, would I be okay with it continuing like this?”
  10. LISTEN TO YOUR GUT. You know that nagging voice inside? Yeah, as much as you’d rather not listen, it KNOWS :(.
  11. If it doesn’t open, it’s not your door. Somebody who is into you and wants what you want, will not need to be convinced. They will put in the effort to let you know you matter.

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Jami Goldfarb Shapiro

Jami is a single mom to three girls ages 19, 17 and 12, and the founder of Silver Linings Transitions, specializing in relocation and home organization.