Tag: Dating Advice

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.

How to Identify if the Person you are Dating is Worth the Effort?

two men kissing each other on couch
Photo by rawpixel.com on Pexels.com

I have two answers:

Don’t put in very much time and effort.

Watch their actions and your feelings.

It’s like being a car salesperson and believing every person who test-drives a car is going to buy one. Some people just like test driving cars. They ask lots of questions. Take pictures. Talk about financing. Then they never come back.

You are not a car. You are a wonderful human. You do not have to sell yourself. However, you do have to show some of who and what you are made of. You have to be you.

Just like this other person has to show who they are. If their brand is about finding women to chase them around while they refuse to commit, then you will see that.

So I would not invest very much time and effort in someone who was not asking you to invest time and effort.

Stop and wait and see.

He is worth it if he calls you (or texts or emails.) He is worth it if he makes plans, is on-time, focuses on you, treats you well, and then does it all again for another date and doesn’t do it with other women (after a couple of dates.)

One date cannot tell you what you need to know about a human. You need lots of dates. But you should not be investing time and effort.

And then you need to feel your feelings. Are you trying too hard or desperately needing his attention or do the good vibes flow both ways? I am not saying it won’t be heart-wrenching.

I had an adorable, awkward conversation with my now fiance because he wanted to make sure that I liked him back. I was giving all the go signals, but not totally throwing myself on him (like apparently, a million other babes were).

He asked. I answered. And we talked every day. And from that day I never had to ask where I stand with him. He tells me and shows me.

He mentioned being exclusive first.

He mentioned taking down his profile first.

I was patient and kept dating (which sucked because I literally could not even think about being with anyone else after our first date) until he said the words to let me know he was worth the time and effort. And then he kept doing it.

Ok so actually, new answer. If you have to ask, the person is not worth it. Gut check. Flaky, vague, asshats are not worth it. Find someone who shows up every day and lets you know they care.


Coach JJ

Common Online Dating Mistakes

I get questions about dating mistakes all the time and have written about it frequently, so I will be short and sweet. In relation to online dating profiles there are 3 common mistakes:

  1. Bad photos (or no photos)

  2. Random or rambling bios

  3. Negativity

Now, WHILE actually dating, there are a million mistakes, but these three will leave you dead on arrival.

The first two are self explanatory, but that doesn’t mean do it without help or feedback. Good photos does not mean selfies. Authenticity doesn’t mean saying every random thought you’ve ever had.

Negativity is a bit harder to navigate because you think that you’re being real or honest or open. I see men who are emotionally closed off because they are terrified of being used or tricked. They have all of their defenses up and it backfires. Maybe they haven’t done the work yet or maybe they are really scared, but either way, being defensive is a mistake.

Other negative issues included m women who are too bossy and mean. I think we can all work on being more cheerful and kind, even when men make tiny mistakes. I see women who are all about the money and it makes them ugly.

A healthy amount of curiosity and flexibility is useful in dating. Another mistake people make when dating online is thinking they have all the answers or that they know how it is all going to work out.


Coach JJ