Gentleman Scholar

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 (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?


Thank you for your question. 

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.

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.)? 


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.

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, 

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. 

Etiquette question: You text someone an invitation to a sporting event and you haven’t heard back for an hour. Do you go ahead and extend the invite to someone else? After what interval is this acceptable? Do the rules change if it’s a date situation and not just a platonic men-only night at the Rockets game?

Benton L.
Solipsistic Inviter

Thank you for the question, Benton.

In the circumstance you describe, I’d suggest following the text with a phone call if you’ve heard nothing within an hour: “Hey, buddy! Maybe you’re too busy [jovial reference to aberrant sexual behavior] to check your texts, but it’d be great to see you at the game. Please get back to me pronto ‘cause if you are unable to fulfill your responsibilities, I’ll have to give your ticket to the first runner-up. … “

In general, however, it is more efficient to send a group email or text in this circumstance, offering the seat to the quickest draw. This practice offers the side benefit of potentially instigating a post-game group outing, allowing you and a circle friends to cry into a pitcher of beer after a regular-season loss, for instance, or, in the event of a playoff victory, to rendezvous for a riot.

When asking out a date at the last minute, err on the side of conveying the impression that you would very much like to see her and her alone. (Exceptions exist, however. As we all know, some romantic dynamics are such that it may be preferable to feign extreme casualness or to foment jealousy.) In this instance the invitation does not expire until the pre-game warm-up is underway. Safeguarding against the lady’s tardy demurral or total radio silence, you should have a close friend (close enough that you can tell him he’s Plan B without giving offense) ready to “fly standby”—to grab the proverbial breakaway pants by the inseams and come off the bench to join you.

Dear Gentleman Scholar,

What is the best treatment for 3 a.m. existential panic? Symptoms vary, but in my case it consists of recalling what I was doing 15 years ago, noting that it feels like 15 days ago, then doing the math on how old I’ll be in 15 years and realizing that, subjectively, I will be a doddering grayhead with a colostomy bag full of regrets in about two weeks. It makes it hard to sleep. What can you recommend besides Scotch?


Thank you for your email, Tim. 

I’d suggest you investigate cognac, armagnac, and other venerable brandies. You might also consider reading, remembering, and repeating, like a non-mantra, the first paragraph of The Information

Doing so is somewhat likely make you feel less alone. If doing so makes you feel more alone, then at least the recitation will lend an intriguing weight to your intensified feelings of alienation, and at best the intensified sensation will be of a strength to force your crisis to a moment of total nervous collapse demanding total and immediate renewal, as if ab ovo.

Where did you get your style? It’s so overwrought that I couldn’t read your article on Mother’s Day. But aside from your awful writing, the idea that the holiday is “stupid” says a lot more about you than about anybody’s mother. Do you have any plans to deal with your anger issues?

Margot Fernandez
Tucson Liberal Christian Examiner

Thank you for your inquiry and for your concern.

I got my style down at the crossroads, upon a moonless midnight, after chatting about high modernism and poststructuralist theory and euphony and rhetoric with a sulfur-scented fellow sporting cloven hooves. 

My plans for dealing with my anger issues, Margot, center on getting together with your mom and [jovial reference to aberrant sexual behavior]. 

I’m clueless when it comes to paying for meals. When I go out with relatives, they sometimes pick up the tab, but I never do. When I visit friends, they sometimes pick up the bill; when they visit me, I usually don’t. It’s not for lack of trying. I usually find myself re-enacting the same ineffectual embrace of my wallet as I did in college, when friends’ parents would take me out, and treat me not only to a free meal but also to a scoffing dismissal of my offer to “help out.” I feel awkward every time the bill comes. What to do, Gentleman Scholar?!


Thank you for the letter, Jon, and for your hospitable intentions.

If you anticipate resistance to your insistence on footing the bill, then head ‘em off at the pass. Arrange to pay the tab before it is tabulated. At some point between the arrival of the main course and the demolition of dessert, excuse yourself from the table (“Excuse me. I need to [check in with the sitter]/[scope the sundae bar]/[shoot some H]”) and stealthily deliver your credit card to the server, with polite instructions to charge the total. Sign the slip at the table with a think-nothing-of-it grin. If it emerges that your dinner partner would be offended if you refused to let him “help out,” then let him cover the tip.