Sandy’s Dating Story: Real Advice from Real Dating Stories

I met Sandy on vacation in a tropical land. She was my AirBNB host and I arrived at the island after what seemed like days of travel. She was instantly my vacation bestie and after getting me tucked into my gorgeous room with a view she enticed me to find my second wind and go out for just one drink. I was thoroughly exhausted but I could not pass up her sweet smile and charm. And I am so glad I did not pass it up.

We went to a cute little bar in town where a local band was playing. She drove, I chatted and so we were telling tales. She was divorced with children and although she worked part time at her son’s school she also ran two businesses. Smart, cute, fun. She was the full package.

So it turns out the dude that was singing in the local bar was the one she had her eye one. Also turns out he was married and toying with her.

WTF Sandy!?! Girl you are way to pulled together to be putting up with that crap. Well, then it all comes spilling out – the heartbreaks, the fear, the bad attitude. So we couched the conversation and just enjoyed the music and the free drinks from cheating dude. I offered my services with a vacation special – I’d lounge around while she told me all the best spots to visit and I would repay her knowledge sharing with dating advice.

The first thing I asked is if I could see her dating profile. It was decent – but the lead photo was her hanging on a $100,000 sports car.

Um, Sandy, I thought you said you wanted someone down to earth, like an artist or a poet. This car screams “I want a Sugar Daddy!” She was stunned. It never occurred to her what message her photos were sending. She picked it because she looked cute. Yeah, cute and materialistic. (I’m materialistic, so no shade, just be clear on what message you are sending.)

So then I was curious. Part of he wanted to scream “buy me a Mercedes” and the other part wanted to whisper “read poetry into my ear.” What did Sandy really want? I asked her to jot down a list of top wants in a partner.

She slipped it under my door before she left for work the next morning.

It was two pages long with over 50 attributes! I am not kidding you! She basically wanted James Bond, Thor, and George Clooney, with a little Mister Rodgers and Mrs. Doubtfire thrown in.

Holy God! 50 requirements for a date!?!

And as I started reading I realized that most of them were incongruitous. She wants a CEO who is home early to help with homework. Ok, yeah, don’t we all, but that’s not real life. A partner who is super ambitious might not also be super domestic or super interested in parenting their new partners kids. Them the breaks kid!

Dating is not about wandering around online until your perfect, fantasy soulmate shows up. Nope. It is about having real experiences with real people – flaws and all.

I gave Sandy lots of background on branding and how sales and marketing work to attract the right customers. She hated the idea of putting her business mind to work in her love life, but she knew as an experience business person you cannot be successful targeting 50 types of customers.

Go niche. You hear that all the time. It’s true in dating too. I asked Sandy to narrow down her list to her top three must-have attributes and to relegate the other items on the list to a nice-to-have list. Does it matter exactly what type of job the person has on the first date? Yes you have an idea of what type of person you ideally want to be with, but maybe the housepainter is in law school. You won’t know until you ask.


Self-perception and Dating

I was once asked, “What can be done if there are differences between the way one perceives oneself and the perception that others have?”
I thought it was a great question because this is super important and gets to the heart of branding in dating!
It is really hard to analyze ourselves in any capacity.