50 First Dates—First Date #9 Almost: How To Break Up With Someone You Just Started Dating

How to Break Up with Someone

Dating Site: n/a; met in “the real world”
Stats: Never married, no kids, one dog
Career: Entrepreneur, medical field

I met Red—a fellow fire-top—at a social event I attended with friends. He was sitting at a table next to us with a bunch of his friends. I noticed he had meaty, manly hands—a weakness, so shoot me—and because I’m a shameless flirt, I started a conversation.

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

My two girlfriends laugh at me for my brazenness. (Intoxication-ness?)

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

Red blushes at my compliment. He doesn’t seem to know what to do but glances over a few more times.

“So, are you single?” I ask. “Or are you here with anyone? Come join us.” He’s there with a table of people. I wave him over, anyway.

He joins us.

20Something’s mouth drops open as her head drops to one side in disbelief.

Honestly, people, I was not displaying classy behaviour here by stealing another woman’s potential date, but really, 20Something could benefit if she paid attention. And Red did have the option not to join us.

What do we know? As Mat Boggs coined: Men don’t speak hint.

If you’re interested in a man, he ain’t going to mind you speaking up about how sexy he is. Trust me.

Anyway, I spend most of the night conversing with Red (Note to self: bad friend) and discover we have a mutual acquaintance―his friend the “player,” Willy.

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

Note to ladies: Sometimes a man wants to impress you to show you they’re worthy of you. Take it as a compliment that he thinks you’re all that.

Note to gents: Bragging comes across as vain, shallow and insecure. Be subtle; you’re already worthy.

I give him my business card, and a few days later we start texting, and a few days later we have a date set up, and a few days later I cancel the date.

uh, not my feet

As much as the man is handsome, smart and financially savvy, I don’t think we’re a right fit: I detest the feel of sand on my feet, he loves the beach; I don’t like boating, he lives for the ocean; I loathe beach resorts, yep, that’s his fave; I’m not a pet person, he has a dog; and the list goes on. And I don’t want to lead him on with false hope or take advantage of him with the “proper dinner date” I’d originally insisted on.

I ask if he’d like to go on a hike instead. “As friends.” He says he would. Maturity: check.

Who knows where things could go, but friends is not a bad consolation prize. For either of us.

When to Break Up with Someone You’re Dating Takeaways:

  1. As soon as you know you’re not really 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. If you have been on two or more dates, the classy thing to do is a phone call.
  4. If you’ve bumped nasties, you need to break up in person. 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 that if you take the classy route, she might recommend you to her sexy, single friends. Unlike your friend, Willy.

Ladies and Gents: Let’s not get our knickers in a knot if the person isn’t into us, whether it’s (almost) the first date or if it’s the fifth! Hello! That’s what dating’s about—discovering whether or not we’re into the person. We’d do all a favour (most notably ourselves) by not assuming the other person wants us or expecting the other person to want us simply because we’re on a date or we like them. #getagrip

xo AJ #uncensored

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About the Author Anna Jorgensen

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

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1 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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