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

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

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

Dating site: POF (I think) then Facebook 2010 (!) with a follow-up last week (!!)

Stats: Early 40s, no kids

Work: Building / Architectural Designer

I have no recollection of chatting with Seattle Sailor, but it was six years ago after all.

I scan through his Facebook photos―mostly artsy images or landscape photos―and find one image of what I imagine must be him.

He looks dapper and non-Shreddies-Killer-y, so I reply to his message.

My brief geographical long distance dating history:

When he was living in Vancouver, I was living on Vancouver Island.

Then I met a guy and moved to Seattle (rolls eyes at self).

Then that guy, The Fibber, and I broke up, and I spent my time driving through Vancouver on my way back and forth from 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.) Yadda yadda.

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

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

  1. Which of you is ready, willing and able to move (eventually)? If you want to wake up together consistently, um, no, thinking that your geographical location will work itself out is not something to be “hopeful” about. That’s juvenile thinking.
  2. Do either of you have children or other dependents?
  3. Do either of your finances allow for the portable one to move without undue money or emotional pressure? And will the partner who is financially responsible for both be up for that responsibility? For how long?
  4. Will there be immigration considerations? This is not the time to be naive. 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 real 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?

Back to the Sailor

Nonetheless, Seattle Sailor is in town for the weekend, so we go for lunch.

He’s a handsome devil and intelligent: he used at least three words that I’ll be Wikipedia-ing later. (If I can remember them.)

The food is yummy, and the café’s architecture appeals to his work interest (Homer Street Cafe). Chat is easy.

We talk about the Vancouver real estate market and some of my favourite sentimental haunts in Seattle.

Seattle Sailor doesn’t live on a boat, but he might want to. I don’t.

He’ll be in Seattle for a few years, at least, maybe forever. I won’t.

But we do both like morning smoothies.

I have a great gal in mind for him. In Seattle.


  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. Stop taking it so damn 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 your sensitive ego and act like a grown up. Even if she disappears for years.
  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 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 and act like a grown up.
  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:

Go through your social media connections and, uh, connect with someone new-ish. You never know where you’ll wind up. #roadtrip

p.s. I also dated a man in Vancouver when I was on Vancouver Island. I am well-versed in long distance dating! Oy.

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

Dude, you really do 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 my dating advice to work for you.

Follow my dating advice for shy guys & introverted men and before you know it you’ll get a girlfriend and be cuddled up on the couch chillin’ ‘n Netflix’in with your soulmate — no more Hands Solo!

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

xo Anna

Founder of Wingmam, Lover of Love, Your 2nd Biggest Fan!

You got this.

Um, yeah, here’s the fine print:

DISCLAIMER: Anna is not a psychiatrist—no way—or medical advisor—nope—you are responsible for your actions and the results thereof. Such is life.

About the Author Anna Jorgensen

Vancouver Dating Coach for Shy Guys & Introverted Men. Matchmaker Liaison. Founder: Wingmam

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