What I wore on first dates. I often snapped a picture of what I was wearing so I could be picked out in a crowd. What to wear was at first stressful, then by the end I felt happy and confident showing up as I am.

My First 48 Dates Middle Age & Single

I hit a milestone last week that hit me by surprise. Since my divorce I have been on 48+ first dates.

I know this because I always take a picture of what I look like before heading out with someone new. It started as an efficient way in the age of meeting online to spot me in a crowd.

Then it became a journal of growth.

My first date was out at a random Mexican restaurant on the Las Vegas strip. He was nice enough. It felt forced. He was newly single as well. Now as friends we admit there was zero physical chemistry.

And on and on it went a chain of men as I pushed myself to stay out there and explore the possibilities my life could offer in this way.

I was not perfect. I am the wrong woman for most men. I developed crushes. I learned to play the games of intentional assholery you are expected to perform while single.

There were the dates I lacked the skill to at first say to them that I was not feeling it. Finally I spoke up and looked a man in the eye and said “I am not feeling any chemistry here.” He looked at me and said he was relieved too.

Among the dates were a few that terrified me. I summoned the Uber and was safely in the car having left a $20 with the bartender before texting that I was gone.

I gained confidence both as my weight dropped by over 80 pounds and my ease with the process that most are just looking for tonight. Those with other aims are not ever going to express them quickly by middle age.

I knew the rules and broke some. Especially the part where you are supposed to be aloof with zero enthusiasm for meeting someone you find awesome. I have texted too long and too often. Then I usually give up as they say you should.

Those I date more than 3 or 4 times become fodder for chats with my friends as I aimlessly wander. Those who strike my curiosity get nicknames for brunch conversations which I assign with glee: GungaDude, Back-Atcha, Fonz, Bad Idea, The Cult Leader, Fiddler, Jim Journo, and Cheaper Charlie are characters worthy of their own tales.

Here are the lesser known things I learned:

  1. Men don’t want to hear how big your balls are and how you could crush theirs. Dick measuring contests make for bad dates.
  2. Figure out early if he can pay his own bills. Now women are viewed as potential sugar mommas and I have no interest in that. You don’t need to be rich. Just have a life you enjoy and have made the correct adjustments to afford.
  3. It’s not exclusive until it’s exclusive. Stay out there. You may have met a man you really want to know better, but unless and until he makes an effort stay out there.
  4. If and when a man texts back has zero correlation to really how busy his life is at this moment. The pandemic taught us all that. I work strategically in human behavior as my career. I know its leveraging, lack of energy, or fear. None of these things are mine to correct.
  5. Dress for what makes you happy. I love to look pretty so I do. But I also give myself permission if it strikes to show up in jeans and a sarcastic shirt if it’s just for a get to know you drink.
  6. Weekends have a ranking system. Nicer folks reach out to who we are most interested in around Thursday or Friday and hint at getting together. The truly inconsiderate have a story on Sunday afternoon and want to come over but have an early morning on Monday. Abject assholes call after 8pm Sunday.
  7. You will find there are those who are just weird period. If you have not met one then YOU my friend are the weird one.
  8. Never, and I mean never answer the question “what are you looking for?”
  9. By middle aged everyone knows what is broken, and they are not looking to be fixed. Most have lives of intention they are not seeking to change. So breathe in that moment in time. It does not need to be anything more than that moment.
  10. Play nice. Everyone else won’t necessarily. But you should.

The adventure continues……

I go on 1 date a month with someone I don’t know yet. It’s growth. Men I have been out with before are free to call me. I actually prefer it that way because I know them. I don’t hold my breath.

Foolishly skirting desperate I continue to touch back to those who I am curious about in instances where there has been no resolution with months between dates.

Live and be fierce.

It feels like you don’t show up as the same person to any two first dates. These are shots while on dates or about to go meet a date. What I wore. Its trying who you are in different company for good or bad.



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