Jillian @jsambold
P.S. I Love You
Published in
4 min readMar 3, 2016

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Contrary to what the outsider might assume, the dinners, drinks, and conversations with all of my first dates here in California have been well worth my time. That’s the honest-to-goodness, no-sarcasm truth.

Who wore it best? My date that day or this random girl at the brewery?

To all of you, spanning San Francisco to San Diego, thank you for the lessons you’ve unknowingly taught me:

I’ve learned my qualifiers and my deal breakers. A lack of honest, intellectually engaging conversation will get a guy shutdown quicker than bro can say “YOLO”.

I’ve learned that “pretty” doesn’t cut it here. Just like Rio de Janiero, the most beautiful people on earth are a dime-a-dozen in California. You’d better have a solid elevator speech and a catchy je ne sais quoi if you want to be wined and dined.

People can be selfish in relationships (myself included). It’s not until that pivotal shift when both parties put the interest of their relationship before their own individual needs; that’s when you have something truly worthwhile. Until then, I’ve learned from some of the best gentlemen I’ve met out here: be good, be generous, and openly be yourself along the way.

I’ve learned it takes 90 days to begin to truly get to know someone. Ladies be warned: A guy told me once, in the world of online dating, your profile just gave a free lunch to that guy with bad intentions. He knows exactly what he needs to say to win you over. And think about it, any jerk can open a car door for you too, ladies. It’s not difficult.

That said, I’ve learned to watch for red flags: I met a cute guy at an upscale nightclub who was a developer for Twitter. He talked a pretty good game, until he mentioned he didn’t have a car. Living in La Jolla without a vehicle? Okay, if this was New York, yeah sure. San Diego, though? Smells like BS to me.

I’ve learned where men perceive women on the “Crazy/Hot” matrix is directly correlated to what they are going through in their lives at the critical “first impression” moment. Hence, it was very stupid of me to attempt dating when I first moved from Ohio to California, was working 60+ hours per week, learning a new industry, trying to buy a car, moving for a second time, buying major appliances, legally changing my name, missing my friends and family, and the list goes on. Now I just look back and laugh! Lesson learned.

I’ve also learned the “Cute/Money” matrix works in the inverse! Hot surfer bums and those seeking citizenship absolutely love an established woman.

I’ve learned actions will always speak louder than words. One of you talked some heavy talk about meeting your parents a couple months into seeing each other (!) but then no sign of affection in front of your crew? Peace.

I’ve learned that some people just need an ear and and an unbiased perspective. We’re all at different points in our life stories. Just because you don’t feel a romantic interest in someone, doesn’t mean you can’t benefit from having met one another.

That said, genuine interest in other people can easily be misinterpreted as “she is so into me.” So I’ve learned to watch out not to send mixed signals!

The man of your dreams isn’t necessarily the man for you. There was only one guy I legitimately fell for out here in California, and it was just because I thought he was everything I’ve always wanted. Turns out, he was no different from anyone else. It was the best lesson in the bunch, hands down.

Lastly, I have to laugh because I’ve learned I have Peter Pan syndrome as bad as most of you California boys do! And I’m not sure if I’ll ever really “grow up”. Two years out of my divorce and I thought I wanted a relationship again. But I realized the truth is, maybe right now I don’t. I love the freedom of picking up and taking off whenever I feel like it (Hellooo, Barcelona next month!). I love having my platonic guy friends without question. I love my adventures and the stories I’m crafting with my experiences every day.

So even though you guys may never be more than a first date, I’ll continue to enjoy our laughs and fleeting time together. Hopefully I’ve given you as much as you’ve given me.

This post is dedicated to an amazing, newly-single friend of mine. May your quest into the wilderness of adult single life be even more incredible and eye-opening than mine has been.

Did you find this valuable or enjoyable? If so, tapping the little heart in the bottom left or sharing this post would mean a lot to me. Thanks for considering! @jsambold

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Jillian @jsambold
P.S. I Love You

Extroverted introvert & eternal optimist. Long lost writer getting her sea legs back. If something I write makes a difference to just one person, I did my job.