Agony Aunt: “I’m a softboi—I need pretentious chat up lines!”

A man sitting on a yellow sofa working
“Oh feculent one, may the buttresses of my loins illuminate your whimsy for the sake of frivolous abnegation.”

Ah, the softboi. That special type of human male so in touch with his emotions and intellectual side, it makes him a massive tosser.

Still, we don’t discriminate even against tossers here. So, we’ve ruffled our pretentious prose feathers and are ready to delineate within the spheres of ideational romantic entropy.

Articulation Towards a Demoiselle

Salutations! Hail and well met, good sirs. I am Jeremy. Of late, the paradigm and synergy I muster is not of, pertaining to mine dating requirements, of coeval anthropoids in female form, resulting in a cessation on rambunctious interactions. 

Therefore, I appeal to you today—hence, this message. Here and now. The susurration and suppuration—the mordant and plangent, obstreperous need for me to pitter-patter and dally at women. 

Ethnography. Diffidence. Nescient. Prescient. Substantive amelioration of milieu, per se, methinks, upon which I have ennui. I am aquiver... I must bed babes! Persist to assist me, for which I am obliged. Regards, Jeremy

Hello, Jeremy. Thanks for the mansplain regarding your predicament.

Aquiver you may well be, but until you calm the bloody hell down we can’t help you, man! Are you calm!? Good! Here are some ideas for you.

Softboi Assistance

The purpose of being a softboi is to rant inanely and hope most of the stuff you cobble together makes sense.

Yet, if it doesn’t, it’ll be such a confusing hodgepodge of bollocks the reader/listener will be baffled and presume you’re some sort of misunderstood genius.

If you can master this, then women will hurl themselves at your feet in astonishment at your ability to articulate beyond, “Oi oi, darlin’, you’re well fit, you are. Wahey!”

Pretentious Chat Up Line Advice

You should learn as many pretentious words as humanly possible. Remember these key softboi things, too:

  • Your favourite band is Tame Impala.
  • You’re a messed up maverick—it adds to your allure.
  • Drugs are a thing for you—probably heroin. Also, chamomile.
  • You know you’re vastly superior to whomever you’re trying to chat up.
  • Always point out some flaw with the dame you’re chatting up, to bring her down a peg or two. Then smack her one with your intellectual might.

Also, purchase a copy of Simone de Beauvoir’s The Second Sex—carry it around everywhere with you, even though you’re not going to read it.

And… embrace the ellipsis. It adds dramatic heft. Combine that with the above and you’ll have great pretentious chat up lines. Such as the below:

  • Darling, you are a vacuum cleaner in the vamoose of my soul, sucking the musculoskeletal alterity from within to create an elision of romantic condensation that forms a hybrid of melioristic precipitation for which… we can get a coffee together.
  • I have the handsome hubris to know you are boondoggle… a beautiful boondoggle. And I shall bark and wag my tail until you pat me and you become man’s best friend. Woof woof.
  • Your nose reminds me of the facinorous and farinaceous Wicked Witch, by which I imply, or apply, you’d melt if I covered you in water. Tea or coffee? Or both in a cup? Thus confirming your wicked desire to merge me, with you, from which we’ll become a silky merger of a caffeine crush.
  • Send me nude pics. I won’t judge harshly. Sorry if this sounds preachy. I am on smack… and pining for your response in the way a male stripper greases his g-string before a particularly arduous performance. I am your Chippendale, but we’ll never dine at a chippy. Only the finest gourmet burritos for you, mine darling.
  • You are my Catch-22. Your lack of integrity is clear and you are clearly not worthy of mine time… but, ludic milquetoast of aesthetic superlatives, you are blessed with “good looks”. Meet at mine for heroin, cuddles, and a viewing of 500 Days of Summer?
  • You and I are fait accompli. I with my stash of illegal heroin. Not I (you) with your daddy issues. Do you need some tissues? Let us fuse, shmooze, and you can become my muse. I am the beacon of prolixity to infuse within thine rapidly declining good looks due to the savages of age. Join me before it is… too late, to tempt fate. And before even I put on weight. Although I already have gout.

There you go, Jeremy, some templates you can adapt there. Best of luck.

And remember! If you’re a softboi, taking up softball may also assist you in your mission towards a morally bankrupt state of mind. Or it’ll teach you about team spirit. Or something.


  1. Excellent advice! The “boondoggle “ line is sheer perfection, I’d pass on the savages of age though ( at least not out loud) that won’t get softboi anywhere. Heroin and cuddles., the perfect date!

    Liked by 1 person

Dispense with some gibberish!

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