Are My Flirty Texts to Female Friends Too Flirty?

Sensible answers to the questions of modern manhood.
July 31 2013 7:30 AM

Are My Flirty Texts to Female Friends Too Flirty?

My girlfriend thinks so.

Troy Patterson.
Troy Patterson

Photo by Christina Paige

Please send your questions for publication to gentlemanscholarslate@gmail.com. (Questions may be edited.)

Dear Gentleman Scholar, 

Recently, my girlfriend read my text messages and found flirty texts between me and my female friends (that issue is another convo). She became mad at what she thought were flirty messages: things like "<3" and "What would I do without you ;)?". 

I understand my girlfriend's logic; she feels undifferentiated among all the girls I say sweet things to. Am I in the wrong?

Sincerely,
Paul

Thank you for your question. 

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As we all know, Paul, it is possible to flirt—to flirt hard, with intent to enrapture—while employing superficially innocuous language. Given certain contexts and subtexts, correcting an interlocutor's who to whom might strike a chord like a tortoise-shell plectrum stroking chromatic vibrations from the tight strings of a goatish lute. Shall we explore the issue today? No, we shall not. That truly is an issue for another convo, unlike the issue of your girlfriend's surveillance program. In fact, her reading your text messages is of a piece with her critical reading of the text of those messages—expressive of paranoia. The vast majority of so-called harmless flirting is correctly called so. The sunny expressions of fondness you reproduce above are by no means actionable offenses. Had your girlfriend discovered an intense amorous confession or anatomical comment, she would have been well within her rights to bring you in for questioning. However, the situation is reversed, and you should strongly consider pressing her to discuss her troubled suspicions and troubling suspiciousness.

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When is it inappropriate to wear a three-piece (as opposed to a two-piece) suit? Is it sometimes wise to dress at or below the level of those around you (not just co-workers, but corporate superiors, high-ranking elected officials, etc.)? 

—Alexander

Thank you for your question, Alexander. 

I would avoid wearing a three-piece suit anywhere there might arise the disharmony of reasonable people finding the look off-puttingly haughty or offensively highfalutin. 

Now, as we all know, the three-piece suit originated as an outfit indicative of simplicity, sobriety, and thrift. On Oct. 7, 1666, when Charles II declared it the official dress of his court, he was reacting against the ruffled frippery rendered fashionable by Versailles, reining in extravagance, and suggesting modesty as the proper sartorial response to the aftermaths of the Great Plague and the Great Fire. But hey, that's irony, and these days it is considered a bit snooty even to use the word waistcoat

Think thrice about slipping into a vest in certain circumstances, such as when interviewing for an entry-level job, appearing in a courtroom where your fate sits in the hands of your so-called peers, and traveling to the rural Midwest to foreclose on a family farm.

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Hi Troy, 

I know you're here for the men, but I value a man's straightforward opinion and would appreciate your advice.  

A colleague and I have been having lunch weekly for a year, sometimes alone but mostly with other colleagues. He often pays, opens doors, pulls out my chair, and brings me my favorites from the buffet. Recently we attended a conference, and when I insisted I cover something, he said in front of colleagues, "You keep offering, but no way I'm letting you pay." We don't hang out outside of work functions, so it's not one of those do-dating-stuff-but-not-actually-dating situations, but we make each other laugh, and it's clear the spark is there. 


He's introduced me to his adult children (they've friended me on FB), and I know he's not playing games. He's older (66 to my 50) and just finalized a hard divorce after a 30-year marriage. Told me he won't be ready for a serious relationship for a long time, and I understand. He's a gentleman whom I admire, respect and am crazy about, which I've told him. There's no issue with our age difference, and his best friend told me he finds me attractive, intelligent, and "a great gal." He considers me a dear friend, and I'm wondering: Once stuck in the friend zone, will it be possible to get out? 

Thank you, 
DCL

See now, this is flirting. Dear lady, thanks for asking, but you are most definitely not in the "friend zone." You have succinctly enumerated the reasons that this tasteful fellow might deploy a slow wind-up when pitching woo. 

(I am tempted to guess, also, that the fact of his age also determines his pace. I'm not talking about the age difference; as we all know, the half-the-your-age-plus-seven-years rule remains a useful guide for charting the outside limits of good taste in dating—or tumbling around on the folded futon mattress of—people outside one's immediate age cohort. I'm talking, rather, about the fact that you are being courted by a gentleman who likely began his dating life before the sexual revolution kicked in. There could be a Rip Van Winkle issue.) 

Try to be patient. When you get impatient, initiate a gently escalating campaign of sassy remarks and saucy behavior. 

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