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

Dating site: POF (I think) then Facebook 2010 (!) with a follow-up last week (!!)
Stats: Early 40s, no kids
Work: Building / Architectural Designer

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

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.

Our brief geographical 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.)

These are the biggest questions a sane person actually 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?

Nonetheless, he’s 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. Ladies, if you don’t click today or he disappears for a while, life has its winding turns, and he may be back in six years. Stop taking it so damn personally if the timing isn’t right right now. I know ladies who get all pissy and hit delete as soon as they receive a slightly delayed reply, like maybe he’s in the shitter for five seconds―have you thought of that? In other words, get over your sensitive ego and act like a grown up. Even if he disappears for years.
  2. Gents, 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. Ladies and Gents, 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.

Know someone thinking of a long distance relationship? Share if you care! Pass this along. 🙂

About the Author Anna Jorgensen

Dating, Love and Relationship Coach Founder: Wingmam, Vancouver, Canada Warning: Not PC, not a feminist ❤️

Leave a Comment:

Mark Yamabe says August 7, 2020

Stumbled upon your videos. You have a unique and fascinating style and, you’re cute and funny. I wish you success!

Matthew Warburton says September 12, 2020

Hi. I am in a LDR with a Filipina. Maria. Have been now for 11 months. I am in England and we cannot meet until December 2021. She is an amazing girl. I am crazy about her. I plan on going there for about 40 days maybe a little more. After that we plan to get her a UK visa. I don’t know what the future has in store for us but I know I want to next to her no matter what.

    Anna Jorgensen says September 14, 2020

    That’s a long time to wait! I hope you’ve met in person, at least. If you haven’t already watched my video on long distance relationships, you can find it here. Good luck! 🙂 xo AJ

    By the way if you’re mistakenly subscribed to my women’s blog, you’ll find my men’s blog here.

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