How to End Your Summer Fling…

In Toronto, it’s kinda known that “Summer” is not over on some random day in September…it starts its descent after Caribana and comes to a full stop on the last day of the Ex. So when Summer ends, so does the “Summer Fling”…

*innocent face* Oh, you didn’t know that we know about this? Tsk tsk. Oh hunny bunnies…of course we do. Your M.O. is as follows:

Break up with the “Winter Fling” around March (March Madness gives a lot of you an excuse to be distant, doesn’t it?). You cast around (i.e. date, hookup etc) with various girls until you find the one that “clicks” (i.e. gives great booty and you’re not ashamed to take her out in public). You then take her to BBQs, rooftop parties, the beach…hell, you might have even done a long weekend getaway with her. Then you two start to talk about the days after Labour Day…much in the way your Winter Fling talked about plans after Valentine’s Day. She mentions that her coworker is having a late September wedding…you nod and say “cool” while thinking.

Faaaaack. What’s my exit strategy here?

You with me so far? Good. Because what I’m about to write requires your full attention. Press pause on iTunes, turn down the volume on the TV, tell your boy to stop talking…

For the love of all that is good and holy, do not – I repeat DO NOT – drop off. I don’t know who is telling you that “going dark” is a good break up tactic, but please stop listening to them. Better yet, send them to me so I can smack them around a bit (and not the way they might like it). I know, it’s the only thing you know how to do after years of conditioning, but I want to help you fix that. So, before she starts talking about the Fall wedding (a.k.a the event that would take you from “dating” to the “decision”), here are my tips for ending a relationship without looking/acting like a complete punk.

How you end it is based entirely on how you started it. Did you establish that this was a summer fling? No? Bad move. I’m not saying that this will make the ending any easier but it gives you an irrefutable point when she argues it. When she relays the tale of the breakup to her girlfriends, the pragmatic one (e.g. me) will say “but he DID say he wasn’t looking for anything serious, that he just wanted to have fun this summer”.

So, assuming that you didn’t (because so many of you don’t), you need to start talking about your other commitments – work, school, your fantasy football pool, whatever. Anything that says “I will be committing to something else after Labour Day, it just won’t be you…”

Now that’s a bit of subtle hint, so she may not pick up on it. Be careful, you cannot sound like you are complaining about these commitments because she’ll think you’re trying to bond.

So, then you need to move to stage two…

Slow down on the sex. I know. This is erm, hard, but you must. You see the whole point of a fling, regardless of the season, is the guaranteed sex…take that out of the equation and you’re left with…not much. This also means sleeping over less, less cozy “morning after” brunches blah blah blah. When she questions it (and she will) this is when you can invoke that list of commitments – work is ramping up, you got to get more disciplined with your workout schedule, etc.

Use Social Media to your advantage – this is how you give some validation to your list of commitments. Update your LinkedIn profile…on Facebook, talk about the end of summer blues and post “all good things must come to an end” on your wall. Get excited about back to school shopping even. Just start talking about the end. BUT DO NOT USE IT TO BREAK UP WITH HER.

Other things you shouldn’t use: text messages, GChat or emails. I once had a Fling get spooked about being in a relationship with me and dump me via email. On my birthday. He then showed up at the party. You know what he did before that? The fucking “drop off’. Dumbass move.

Make plans. Without her. Then tell her about them. Head out of town with the boys for Labour Day or something. She’s gonna get stabby when you do this, but that’s when you can say “we do this every year so that we end the summer right”. But this – and this is important – you have to really go away or not leave your house for the entire weekend. Because the chances that you will be spotted, by her, at the same party that weekend are very very high. Or, someone will just tag your dumb ass on Facebook.

True story…dude then came to me asking how to do damage control. My advice was: “move out of the city, dumbass.”

Here’s one you won’t like: Man up and tell her. You have to have the talk. Be honest (you remember how to do that right?) Again, do this in person. Do not speak in generalizations, get to the point fairly quickly, but not right off the top. Don’t do this in neutral territory…

Wait, what? Yes. Do it privately. In public, you can’t talk about how great the sex has been. Since you’re doing the dumping, you need to be clear that it’s your issue and not hers.

Just don’t say “it’s not you…it’s me” (because I will hunt you down and kill you). I know…I’m not leaving you with much to say am I?  When you have the talk, this is what you need to point out:

“I don’t want to develop a relationship with anyone right now. The truth is, you’re a wonderful woman  – funny, smart, amazing in bed, gorgeous. But I’d be wasting your time if we continued any longer. Things have to progress and while I’d love to keep seeing (i.e. having sex with) you, I would probably hold you back from meeting a guy who’d be lucky to call you his girlfriend. I’m just a guy who wants to have fun.”

She’ll do one of two things:

Call you a fucking asshole. De-friend you from Facebook. Screen your calls. Bad mouth you to anyone who will listen. But once she calms down, she’ll realize that if she wanted a relationship, that you really would’ve been wasting her time. You’ll then become an “ex-fling” instead of “the fucking asshole who led me on for an entire summer”.

Or she’ll say:

“OH THANK GAWD! I was worried that I’d have to go out and find a new fling! Let’s keep this status quo, cool? I’ve packed all the stuff you’ve left at my place…and let’s schedule a hookup (whips out Blackberry) next Friday? Oh wait, Friday won’t work – girl’s night out…how about I just call you?”

Breaking up is not pleasant; a “good breakup” is an oxymoron…you must remember that what you’re going to say and your actions after are basically damage control.

If you’ve been managing more than one fling and you’re ready to wife the other one, tell her that. Don’t use any of the other tactics here and then wife the next girl…that’s an asshole move.

Don’t try to end the fling and then ask for breakup sex… breakup sex is for relationships, not flings. Do it the morning after (but before brunch…if you’re hungry go to McDonald’s).

Okay. That’s it. Best of luck and don’t forget to dodge the projectiles.


“So, right or wrong, when a man isn’t confident or comfortable with his financial, career or social status he often hesitates, he may not feel ready to take the plunge…”


I have heard many stories from women (and have a few of my own) about this “I’m not ready” speech.
Yes, we know that you have dreams. Yes, we realize that you may not be in a place career-wise or financially stable or socially set in such a way that makes you feel like you are ready. What we DON’T bloody well understand is why after giving us that “speech” from page 49 of the playas handbook (I KNOW this book exists) do you move on to the next and… voila! You are now ready to settle down.

Even though you have the same job, the same salary, the same education and the social status that you did when you told us you weren’ t ready to settle down.

You know what makes the statement “I’m not ready to settle down…” an honest one instead of a “speech”?

“With you”

I’m not ready to settle down with you.

Then you can list the reasons (to the woman who is going to be angry) as to WHY you feel this way. One of two things will happen: you’ll dump her or you’ll realize that you maybe should stick it out with her. If you dump her, she’ll be mad at you, curse your name, blah blah blah.

BUT if she sees you engaged, shacked up, about to have a baby within a year of breaking up with her (all true stories, one of them mine) then we despise you for your bullshit.

Instead of telling us to eat a dick, maybe guys should stop talking out their asses….

(rant over)


2 thoughts on “How to End Your Summer Fling…

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