Gentleman Thrashing

When you masturbate or get a handy from a woman, in a very eloquent and distinguished manner.

Bro 1: Yo, dawg, what's taking Parker so long?
Bro 2: He's giving himself a Gentleman Thrashing. He'll be out after he takes the tux off.

by NattyChamps2021 July 27, 2022

Gentleman-Gigolo Complex

Essentially the antithesis to the Madonna-whore complex where a woman may be sexually attracted to the dominant and agressive "gigolo" but may not see him as an ideal partner or spouse. On the other hand she romantically desires the mellow and submissive "gentleman" to be a husband and father to her children but may not respect him as a man or partner. The "gigolo" may possess dark human traits that are deemed "toxic" or "dangerous" such as Machiavellianism or could simply just be charismatic, masculine, and attractive, as well as being able to sexually satisfy the woman. Meanwhile the gentleman may possibly possess pure traits including sensitivity, emotional intelligence and even leadership qualities and financial success, but may also be shy, non-confrontational, passive-agressive, and submissive which at worst makes him more susceptible to molding and manipulation and may not sexually satisfy the woman.

Man 1: Did you see that girl Cheri give that millionaire dude her number
Man 2: yeah but she has a Gentleman-Gigolo Complex, and that guy isn't going for someone like her

by TJ May 23, 2021

Gentleman's Flight

A business flight in the late morning (i.e. 11 am) to avoid the crowds and to have enough time to masturbate before going to the airport

Gentleman 1: "Are you sure you're down for another strip club?"
Gentleman 2: "Yeah bro I don't have to get up early... I have a gentleman's flight!"

by CKMeredith June 20, 2025

the gentleman's tip

The sex act where a man, upon receiving a woman's permission, inserts the index finger (no further than the middle knuckle) into the woman's anus during vaginal intercourse, and gently slides this portion of the index finger back and forth.

We find ourselves in the midst of a conversation between Jane and her friend Sarah that has stumbled upon the topic of anal sex, let's observe.
Jane: James has been asking for it forever, I don't know Sarah, like, I think he could be the one. What should I do?
Sarah: just have him start slow, with "the gentleman's tip" and work your way up from there

by JuiceBox89 January 28, 2015

The Honourable Gentleman

The twat from the other party.

The Honourable Gentleman the member of New Forest West

by Luke5045 October 21, 2019

A Gentleman’s Lift

A Gentleman’s Lift is a golfing term and refers to when a ball lands in a difficult spot. The player can move the ball to a more favorable area without incurring a penalty stroke. One club length is the widely accepted distance the ball can be moved, although the distance can vary from player to player.

Mike: “Wow, what a brutal tee shot!! Why did I use my driver??? I never hit it straight!”

Jamie: “Why don’t you just take a Gentleman’s Lift?”

Mike: “What’s a Gentleman’s Lift?”

Jamie: “Pick up your ball from that terrible spot and move it to a better spot”

Mike: “But won’t I incur a penalty stroke for that?”

Jamie: “Not at all, that’s the beauty of a Gentleman’s Lift!”

by Foggy Clue September 10, 2020

Gentleman's Farm

A "gentleman's farm" refers to a property, typically of substantial size, owned and operated by someone who primarily engages in farming for pleasure and recreation, rather than for profit or livelihood. These farms often feature well-maintained landscapes, elegant country homes, and a range of activities, including livestock, orchards, and vegetable gardens.

"He turned his hobby into a gentleman's farm, complete with a vineyard and a petting zoo,"

by SusanB123 May 1, 2025