50 First Dates—First Date #6 (Almost) How to Break Up

How to Break Up with Someone You Just Met…

How to break up with someone depends on how long you’ve been dating.

Basically, the less time spent together, the less formal the break up need be.


If in doubt, always err on the side of classy. If you’re not sure how to break up, level up one notch in  effort.

Dating Site: n/a; met in “the real world” but I’m counting this as date #6!
Stats: Never married, no kids, one dog
Career: Entrepreneur, medical field

Several years ago when I’d just moved to Vancouver, BC, I started a 50 First Dates Project.

I’m revisiting those first dates to update any tips that might help you in your dating life.

(If this is your first 50 First Dates post and want to start at the beginning, click here.)

50 First Dates Date #6

I had met Red—a fellow fire-top—at a social event I’d attended with friends.

He was sitting at a table next to us with a bunch of his friends.

I’d noticed he had meaty, manly hands—a weakness, so shoot me—and because I’m a shameless flirt (when my skin isn’t in the game, at least), I started a conversation.

“Hey, you―” he looked over at me, unsure, and I continued, “Yes, you. You’re handsome. I like your hands.”

My two girlfriends laughed at my brazenness. (Tipsiness?)

The 20Something beauty sitting next to Red gave me the stink-eye, but because I’d already downed one Cosmo (martini) and it’s rare to see a specimen (man) I find attractive, I couldn’t help myself.

Side note: What I find physically attractive in a man isn’t necessarily what society would expect. And noooo, I’m not available and nooo I’m not encouraging you to ask me out. (Please don’t.) I’m sharing this personal info as evidence you, Sir, don’t have to be movie star looks to get a good woman.

Back to the story…

Red blushed at my compliment. He didn’t seem to know what to do but glanced over a few more times.

“So, are you single?” I asked. “Or are you here with anyone? Come join us.”

He was there with a table of people. I waved him over, anyway. He joined us.

20Something’s mouth dropped open as her head tipped to the side in disbelief.

Honestly, people, I was not displaying classy behaviour here by stealing another woman’s potential date, but really, 20Something could have benefited if she’d paid attention.

And Red did have the option not to join us.

What do we know? As Mat Boggs, dating coach for women, coined: Men don’t speak hint.

If a woman is interested in a man, he ain’t going to mind her speaking up about how sexy he is. Am I right, fellas?

Anyway, I spent most of the night conversing with Red (Note to self: bad friend to my crew) and discovered we had a mutual acquaintance―his friend, Randy, “The Player.”

Either because he was shy or nervous or insecure, Red spent a lot of time telling me things likely meant to impress me, but my girl friends thought he was a braggart who was vain and shallow.

Note to gents: Bragging comes across as vain, shallow and insecure. Be way more subtle than you think you need to, she is paying attention, I assure you. Also, you’re already worthy.

Note to ladies (in case there are any here): Sometimes a man wants to impress you to show you they’re worthy of you. Take it as a compliment he thinks you’re all that.

I gave Red my business card and a few days later we started texting.

A few days later we had a date set up.

And a few days later I cancelled the date.

uh, not my feet

As much as the man was attractive (to me), smart and financially savvy (financial irresponsibility makes all women feel unsafe), I did’t think we were a right fit.


  • detest the feel of sand on my feet, he loves the beach.
  • don’t like boating, he lives for the ocean.
  • loathe beach resorts, yep, that was his fave.
  • am not a pet person (I now love certain small dogs, individuals not breeds, and am a cat person but allergic), he had a dog.

The list went on.

I did’t want to lead him on with false hope or take advantage with the “proper dinner date” I’d originally insisted on.

I asked if he’d like to go on a hike instead, “as friends.”

He said he would. Maturity: check.

Who knows where things can go, but the friend zone is not a bad consolation prize.

When & How to Break Up with Someone

  1. As soon as you know for sure you’re not into the person, let them know.
  2. If you haven’t been on a date yet, or only one date, it’s okay to “break up” by text.
  3. But, if you’ve been on two or more dates, the classy thing to do is a phone call. Yes, with verbal words! (Emphasis for the youngins.)
  4. If you’ve bumped nasties, you need to break up in person, unless you live in different cities. It’s awkward, but come on, you knew you weren’t really into her before you got in to her, dude.
  5. If you kinda like each other but not romantically, remember if you take the classy route, she might recommend you to her sexy, single friends. Unlike your friend, Randy.

Last Note, Gents

Don’t get your knickers in a knot if she isn’t into you, whether it’s (almost) the first date or if it’s the fifth.


That’s what dating is about—discovering whether or not we’re into the person.

A first date just means you passed the physical inspection. Remember, women need a lot more than being ok with your looks to consider you for any kind of relationship, short or long.

You’d do all a favour (most notably yourself) by not assuming she wants you or expecting her to want you simply because you’re on a date or you like her.

xo Anna

Remember, you have one shot to make a first impression, so make it a good one!

To make the best first impression on a first date, watch these:

About the Author Anna Jorgensen

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

Leave a Comment:

Anna Jorgensen says September 15, 2016

A comment from a write-in observationalist—my responses in CAPITALS not because I’m yelling but to distinguish my comments:

I was replaying your conversation with Red where you saw the meaty hands—MMM, MEATY MAN HANDS—and also that he was talking to a young lady.  It struck me that his character is questionable if he was willing to leave the woman he was talking with to join you.—HE WASN’T TALKING WITH HER, HE WAS SITTING NEXT TO HER— If you were with someone, how would you feel if he was looking at all the beautiful women walking around Vancouver?—HE WASN’T “WITH” HER, HE WAS WITH A GROUP, BUT I HAVE BEEN WITH A MAN WHO HAD “VALIDATION” NEEDS. I DUMPED HIM.—I get the impression you’d soon be laying out the ground rules, either you or them but not both!—ABSOFUCKINGLUTELY—
The other observation is that you were the other woman that enticed him away.—INDEED—I don’t think you’d be too impressed with either your date who walked away from you or the woman that lured him away.—OH, CONTRAIRE. I’D LAUGH. BUT IT WOULD BE QUITE UNLIKELY THAT I’D CHOOSE SUCH A MAN (AGAIN)—  
For myself, I can easily bounce my eyes as soon as I see the woman is “attached”. —AN ADMIRABLE QUALITY—I don’t ever want to be the “other man” that I’ve heard so many stories about.—IN MY OPINION, THERE IS NO “OTHER MAN” IF THE MAN SHE’S WITH ISN’T INTERESTED IN BEING WITH HER. IN FACT, HE’S DOING HER A FAVOUR.
Maybe this will give you inspiration for yet another blog.—IF ANYONE ELSE EXPRESSES AN INTEREST, I WILL BLOG ABOUT IT!
Btw, are you really happy?   Reading through your stories I start to wonder.—MY MOTHER IS DYING SO I’M SITUATIONALLY SAD, BUT 80% HAPPY, WHICH IS JUUUUST RIGHT. THANK YOU FOR YOUR CONCERN 🙂

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    Anna Jorgensen says January 11, 2021

    Thank you for reading my blogs and watching my videos!

Bruce Wilson says January 12, 2021

Breaking up after anfirst date is a hell of a lot easier than breaking up after three months. How do you tell someone who has fallen in love with you that you are not in love with them and you have to end it? It’s always terrible. Do you have any videos on that, Anna?

    Anna Jorgensen says January 12, 2021

    Breaking up with someone feels bad, but sometimes must be done. First, ask yourself if there’s something she could change that will change your mind. If so, you’re better off to let her know what that is and give her an opportunity to decide if she wants to change that. If it’s something that’s impossible for her to change, obviously you can’t ask for change. Impossible to change example: she has kids, you don’t want kids. Not impossible to change example: she has kids, you prefer to spend more time alone with her. Don’t assume what you think is impossible to change is actually impossible to change/manage. If she’s a good woman, compromise may be possible. Also, don’t feel you have to fall in love with her at the same pace she has fallen in love with you. Is there a potential for you to fall in love with her? If so, the conversation isn’t about breaking up but pacing the relationship and lowering her expectations in case falling in love with her does not happen. Again, then at least she is moving forward with integral information. If you know for sure she’s not the one, sit down and have that conversation. There is no easy way to do this. You’ll have to muster your courage and sensitivity. Good luck!

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