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Dropping Your Handkerchief

Updated: Apr 12, 2023

By: Alessandra Conti, Matchmaker

As a Matchmaker in Beverly Hills, every day I Date Coach beautiful, successful, and smart Bachelorettes of Beverly Hills who are looking for love. The single most common problem that they confide in me when they come in for their Date Coaching Sessions is this: men are simply not approaching them. It doesn’t matter if they are decked out in their most fabulous new curve-hugging dress from Intermix or just had their hair blown out at Dry Bar… they are not approached when they are out at night and are especially not approached when they are going about their daily life, and if they are, the men who are approaching them are either intoxicated or inappropriate.

These fabulous women always come to us asking what they are doing wrong. Is it something in their body language? Are they not making proper eye contact? Is their make-up ok? Ladies, I am here to tell you once and for all… it’s not you. It’s them. There is an epidemic that has permeated the LA dating scene and is ever present within our society called Approach Anxiety. The numbers are staggering: 95% of men experience incapicating Approach Anxiety. Believe me, I am not excusing their behavior. At Matching Up, we are extremely old-school, and we teach each and every man different tools that he needs in his arsenal to overcome Approach Anxiety and build the confidence to approach a woman who he finds attractive. Approach Anxiety does not discriminate; we work with top Doctors to Celebrities and each knows Approach Anxiety all too well. The first step is acknowledging that there is a problem… and the problem is not you (#1LessProblem).

In a utopian society, all men would come into Chivalry Boot camp here at Matching Up and we would whip them into shape. But alas, we can only make the dating scene a better place for our beloved Bachelorettes one man at a time. In the meantime, as women, we must understand that we have all of the power. We must embrace this power and utilize it in the best way possible to get the results that we desire. A disclaimer: we do not condone “picking up” men or chasing potential love interests. Instead, women need to harness our social prowess and simply “drop the handkerchief”.


In the Victorian times, it was socially unacceptable for a woman to begin speaking with a man unless she was formally introduced or he spoke to her first. Women became frustrated with this social norm; after all, a woman’s livelihood, social standing, and future depended on the man that she would marry. Women knew that something must be done, but with such a fragile social system set in place, women did not want to risk the stigma attached to making the initial introduction to a potential suitor. So, these smart, crafty women decided to take matters into their own hands and devised a plan. When they saw an eligible Bachelor, say the Duke of Devonshire, pass by, they would drop their handkerchief in front of him. As a gentleman of impeccable manners, the Duke, of course, stopped in his tracks, bent down, and picked up the handkerchief from the damsel in distress and gave it to her with an “Excuse me miss, you seem to have dropped your handkerchief”. The ice was broken. The introduction was made and women were then free to dazzle him with her wit and charm, and eventually become the Duchess of Devonshire. But in order to do that, the woman needed to discreetly make the first indirect move.

Even though you don’t carry around a handkerchief, you can still drop your figurative handkerchief with a few easy tips:

  • Ask a general, indirect question. When you are waiting in line at the Starbucks or Coffee Bean ask the cute guy in line next to you if the pumpkin spice latte is good. After he divulges his love for all thinks pumpkin, make sure to continue the conversation with a follow-up question. A beautiful follow-up question is, “Thanks so much! Are you from around here?” This then gives him full rein to keep the conversation going. Warning: you may find yourself on an impromptu coffee date!

  • Give a compliment… with a question. Whether you are at the Whole Foods, prepping for a hike at Runyon, or window-shopping at Brooks Brothers, give the handsome guy near you a compliment on an article of clothing, his glasses, or even his tie, and ask him where he got it. Say, “Wow, I love your tie/glasses/backpack. My brothers Birthday is coming up… where did you get it?” Men absolutely love compliments, and they rarely get them, so you will make his day. Make sure you move on to your follow-up question, “Thanks! Are you from around here?” He will take it from there.

  • Ask him to take a photo of you and your friends. Having Sunday Brunch at Toast? Sunbathing with your girlfriends at the Mondrian? At an art gallery opening in Santa Monica? Ask the cute guy walking by to take a photo of you and your friends! The trick here is that instead of snatching it back hastily and scrutinizing your lack of a thigh gap, look down at it quickly and then tell him, “Wow, this is an amazing photo! Are you a photographer?” Once he responds, make sure to counter his response with your trusty follow-up question, “Nice! Are you from around here?” Works every time. (As long as they are not gay or in a relationship).

The secret is to break the ice in an initially indirect way and then be an active participant in the conversation with your handy-dandy follow-up question. Remember ladies: you have the power. You are gorgeous, successful, and any man would be lucky to be your Prince Charming. Sometimes they just need a little nudge.

For more, book a Date Coaching Session or apply to be a Bachelorette of Beverly Hills today!

XOXO Your Fairy Matchmaker,

Alessandra Conti


Matchmakers in the City

This blog post has been reprinted from the September issue of Focus Magazine's Monthly feature: Matchmakers In The City:

Focus Magazine’s Resident Date Coaches, Sister Matchmakers at Matching Up in Beverly Hills’s Monthly Advice for Bachelorettes of Beverly Hills

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