50 First Dates―First Date #7: Long Distance Dating?

Long Distance Dating: “Get My Passport!” or “I’ll Pass, Thanks.”?

Things to contemplate when considering long distance dating or a long distance relationship …

If you’re not familiar with my 50 First Dates Project, well, it’s exactly what it sounds like.

Several years ago, I attempted to go on 50 first dates to find out what men were doing right and less right.

I only made it through nine dates, because I figured I’d gathered enough data to help y’all. Plus, I got tired.

Let’s recap Date #9

  • Dating site: POF (I think) then Facebook 2010 (!) with a follow-up in 2016 (!!) and a one last attempt on his part in 2021
  • Stats: Early 40s (to late 40s), no kids
  • Work: Building / Architectural Designer

I had no recollection of chatting with Seattle Sailor, but it had been many moons ago that I’d met him, after all.

Back in 2016, after he’d reconnected the third time, I scanned through his Facebook photos―mostly artsy images or landscape photos―and found one image of what I imagined must have been him.

He looked dapper and non-Shreddies-Killer-y, so I replied to his message.

My brief geographical long distance dating history:

When Seattle Sailor was living in Vancouver, I was living on Vancouver Island.

Then I met a guy on a dating site and moved to Seattle (rolls eyes at self, see memoir).

Quick side note on Seattle guy:

The Fibber (formerly referred to in my memoir as Handsome But Unworthy American Boyfriend, or HBUAB for short) and I broke up (sorry for the spoiler).

I continued to spend my time driving through Vancouver back and forth tom Seattle because I wasn’t ready to break up with Seattle.

Then I met a new guy and moved to L.A. (Rolls eyes at self again, you’ll have to wait for the next memoir for those juicy details.)

Yadda yadda. Details of this silliness is in my memoir, Me: A Rewrite. (Rolls eyes at self, slaps forehead.)

In 2015, I broke up with Big American Cities and moved to a Big Canadian City: Vancouver.

Back to the Sailor


Seattle Sailor was in town for the weekend, so we went for lunch.

He was an intelligent man and conversationally used at least three words I knew I’d be Google-ing later. (If I could remember them.)

It wasn’t that he was trying to impress, you’ll see why soon, with his language skills, he was just smart, which incidentally does impress me. (Intellectual stimulation is in my Top 5 Must-have’s!)

The food was yummy and the café’s architecture appealed to his work interest.

Chat was easy. We talked about the Vancouver real estate market and some of my favourite sentimental Seattle haunts.

Seattle Sailor didn’t live on a boat, but he thought he wanted to. I didn’t. (Still don’t. Won’t.)

At the time, his work would keep him in Seattle for a few years, at least, maybe forever.

We both liked morning smoothies. (Now, I prefer brunch benny. Note: People change!)

Mistake #1

He let me pick up the tab. #wrongmove

I remember thinking at the time, “Hmm, I’ve got a great smoothy swigging feminist friend in mind for him. In Seattle.”

In case you hadn’t noticed, I’m not a feminist.

I believe in equality but not equity (but that’s for another conversation) and I believe a man should pick up the tab, especially if he invited her!

Even though I wasn’t attracted to him physically, that one move was a total turnoff.

I’m no gold digger. When I was married, my (ex-)husband paid the bills at restaurants and I bought the groceries for home.

I moved to Vancouver in 2015 and sometime after Seattle Sailor moved back to Vancouver we hung out a few times, many months apart with limited contact in between, as friends. (The relevance is coming, I promise.)

We never once gave each other a sign of romantic interest.

There was no romantic interest on my part and I’m particularly conscious of not leading a man on if he’s got no chance, unlike some thirsty chicks.

Mistake #2

Anyway, on one such hang out, Seattle Sailor admitted he’d been wrongfully let go by his previous employer and the company owed him [a f*ck tonne] of loot and he was broke.

But he was not going to pursue it.

Key point: He was broke and needed the money and not going to pursue it!

Does a woman feel emotionally safe or unsafe with a man who doesn’t fight for what’s rightfully his when he most needs it?

Hint: Unsafe!

Even if a woman knows she’s never going to have a family with a guy, she’s wired to be worried about her welfare and those of her unborn children.

Mistake #3

He admitted he wasn’t going to pursue it because he couldn’t handle the stress of it.

Key point: He couldn’t handle the stress of it.

Does this make a woman feels safe or unsafe?

I think you know the answer.

Mistake #4

Because of my questioning, he also fessed up to being a people pleaser.

People pleasers can’t be relied on by any woman because people pleasers are too busy trying to make everyone happy.

Usually, people pleasers please because of a hidden (if subconscious) selfish reason like…

  • Needing to be liked/appreciated/praised etc
  • Wanting something from the other person be it economic/romantic etc

If you see yourself in this description, I encourage you to watch my Nice Guy Playlist at the end of this blog.


After years of intermittent communication and a handful of getting together, Seattle Sailor, recently asked me again if I’d consider dating him.

Aside from my health issues, which you can read about on my personal blog here, I hope you can see why I’d say no, regardless.

Mistake #5

My reply was kind and respectful but because he didn’t get the answer he wanted he didn’t want to be my friend, anymore.

Reality Land: he was never my true friend because he always had a hidden agenda.

When you list the qualities in a true friend, “hidden selfish agenda” and “only if I get what I want from you” are likely not on that list. (If they are, you need more help than this blog can provide.)

If you cannot “do” the friend zone without a hidden agenda do. not. attempt. it!

Read: Benefits of The Friend Zone.

Back to Long Distance Relationships

I know, I totally went on a little road trip with this blog. Please forgive me!

The biggest questions a sane person considers when mulling over a potential long distance relationship are:

  1. Which of you is ready, willing and able to move (eventually)? If you want to wake up together consistently, um, no, thinking your geographical location will work itself out is not something to be “hopeful” about.
  2. Do either of you have children or other dependents and how does that impact who’s moving eventually?
  3. Do either of your finances allow for the portable one to move without undue money or emotional stress? And will the partner who’ll ultimately be financially responsible for both (at least for awhile) be up for that responsibility? For how long?
  4. Will there be immigration considerations? This is not the time to be naive. Especially, post Covid!long distance relationship
  5. Are you really that into the person or do you have artificially elevated amorous feelings triggered by the romantic notion of a faraway lover? Have you spent enough IRL time together to know if you’ll actually like each other in the real world? What’s your back-up plan if you find out your romantic flame fizzles?


  1. If she doesn’t click today or she disappears for a while, life has its winding turns, and she may be back in six years or ten. Don’t take it personally if the timing isn’t right right now. I know guys who get all pissy and hit delete as soon as they receive a slightly delayed reply, like maybe she’s in the potty for five seconds―have you thought of that? In other words, get over it.
  2. If she likes your company that doesn’t mean she’s into you and just because she’s not into you doesn’t mean her beautiful feminist friend in Seattle won’t be. Even if you end up as friends, people still meet mates through friends of friends. In other words, get over your sensitive ego or at least don’t get pissy if the one you like doesn’t like you back. Again, get over it and move on if you can’t handle the friend zone. (Can you handle the friend zone? Find out here.)
  3. Don’t under-estimate the power of Facebook or other social media for matching up with a potentially grown up mate.

Your Mission Should You Wish to Accept It

Become the kind of man who doesn’t make the five mistakes Seattle Sailor made above. Learn to naturally handle life’s twists and turns!


Dude, it’s simple. And almost easy. 😉

You can be a new improved you within five weeks, not quite instantly but what’s five weeks compared to your whole life so far?

WakeUP2Luv: HOW TO GET A GIRLFRIEND OF YOUR DREAMS (Intensive five week online program)

God is your biggest fan and didn’t put you here to be alone and lonely. But, as My Little Mom (RIP) used to say, “God helps those who help themselves.”

You deserve to be loved!

To the very core of me I KNOW this to be true. It is the reason I do what I do.

And, guess what else? You don’t have to believe in God for WakeUP2Luv to work for you.

Follow the steps in the program and before you know it you’ll get the girl of your dreams.

Then you’ll be cuddled up on the couch chillin’ ‘n Netflix’in with your Boo — no more Hands Solo! 😉

Thanks so much for being here in the world with me! For reals.

xo Anna

Watch these and then get my WakeUP2Luv program today!


About the Author Anna Jorgensen

Vancouver dating coach for men who love women! ❤️ (Not PC and not a feminist.)

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