How To Plan the Perfect First Date, According to a Globally-Renowned Matchmaker

One of the world’s top matchmakers reveals how to plan the perfect first date.

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Presented by Valenti Concierge Experience

No matter if you have been on one or one hundred, a first date is inherently intimidating. There are the emotions, first of all: excitement, and the optimism of hanging out with someone you’re genuinely eager to meet. Then the nerves set in. What bar would they like? What do you wear? Will the connections translate to real life?

To help you with these woes, we put together a cohesive playbook for planning a date with the help of renowned matchmaker and venerable dating guru Iréne Valenti. Combining European matchmaking tradition with modern techniques, Irene has been successfully pairing up single men and women for over thirty years.

As part of her Valenti Concierge Experience, she curates your romantic rendezvous from start to finish, planning the venue, transportation, cuisine, and timing based on each person’s needs and interests. Consider her the MVP of making people fall in love; she specializes in curating perfect date settings based on her heartfelt knowledge of singles and the dating scene. You still have to go on the dates yourself, but Irene sets the stage with success in mind.

With the help of her expert knowledge, we’ve laid out the roadmap to a perfect date, spanning how to pick a location, how to curate conversation and dodge awkward moments, and how to follow-up after the date.

Step One: The Lead-Up

So you’ve met someone. After days (or weeks) of great online conversation, how do you suggest you meet IRL? There’s no hard and fast rule for when the right time is to request a date. Take the time to get to know your potential partner, and slide in a segue when conversation allows—if you’re talking about your favorite foods, perhaps suggest hitting their favorite spot.

“Typically, I suggest a dining spot with an ambiance that is conducive to flowing conversation,” says Valenti. “A trendy wine bar or brewery may also be an option, depending on the couple involved.” Save noisy spots or activities for date two. On date one, focus on the conversation: getting to know each other and building a connection.

Do you have your tried-and-true, pitch-perfect, date spot? Maybe the cozy wine bar with buck-a-shuck oysters, or the tapas spot with the perfect playlist? Valenti notes that when picking a date, “Other factors include cuisine preferences, parking, and event or entertainment possibilities nearby are important.” 

Is your date vegan? Skip the steakhouse. Do they have a peanut allergy? Your local Tiki bar is packed with a variety of orgeats and nut syrups guaranteed to take a goodnight kiss off the table. Lastly, while the cute bar around the corner may be convenient to you, look for a locale that is equidistant to both parties.

Since it’s the age of virtual dates, an at-home cocktail hour over Zoom is sometimes the only option. If that’s the case, consider ordering a cocktail kit from a local bar. They could use the support, and shaking up a drink together (if in separate apartments) is an automatic conversation-starter.

Step Two: Pick a Fit and Prepare 

When it comes to picking an outfit, “I don’t believe a man can ever be overdressed for a date,” advises Valenti. “His clothing choices reflect thoughtfulness and enthusiasm for the occasion.”

You don’t need to whip out the suit unless it’s necessary, but opt for something clean, wrinkle-free, and weather-appropriate—your date will appreciate the attention to detail. Have that mentality extend to your grooming regime. A dash of cologne and a hearty swipe of deodorant will combat any nerves and leave an olfactory-driven first impression.

A few rules of thumb: It’s always better to be overdressed rather than under. Flip flops and cargo shorts are generally a bad idea for most occasions unless a dip at the beach is on the itinerary. If you’re prone to sweating, choose a shirt that won’t showcase any stains—muted color palettes are a fail-safe way to make you look put together while hiding any last-minute wrinkles or stains.

“Aside from choosing a nice outfit,” continues Valenti, “Take some time to become familiar with your date. What are some of their passions in life and aspirations for the future, for example? This creates for a more interesting conversation dynamic during the date.”

You don’t need to cyberstalk them, but acquaint yourself with what you know so far. Do you have a rapport or references you’ve built up over your conversations? Do you know what they do for work, for school? Keep any information tucked away in your head—it can come in handy keeping conversation flowing throughout the date.

That said, avoid prescribed, run-of-the-mill questions. “Don’t come with a preset list of questions,” Valenti notes. “The date should involve fun, interesting, and lively conversation and not feel like a job interview.”

Step Three: Showtime

Once your location is set and you’ve done your homework, make sure to show up on time—it will ensure your evening starts on a good note. (Though trains and work emergencies do happen, just don’t make it a regular occurrence.)

Unless you’re an on-call surgeon and lives are at stake, keep the phone off the table. This includes on virtual dates: mute your notifications so your eyes aren’t careening off-screen every few minutes. Being on your phone, or pivoting away from the screen conveys you don’t find your date compelling enough to pay attention.

After that, the key is keeping your mind open. “Every dating scenario is so unique and should be approached with an open mind,” describes Valenti. “No topics should be off the table, so long as both people are respectful and open-minded.”

She advises you let the conversation flow naturally, “versus in a structured, interview-like manner. Don’t monopolize and just talk about yourself—show lots of enthusiasm in coming to know your date and ask lots of questions about them.”

Her secret to keeping a conversation flowing is to “Ask lots of interesting questions that are personalized towards your date and their lifestyle. Don’t get bogged down with the mundane – think outside-of-the-box!”

And most of all, “Be yourself, be open, be enthusiastic, and have fun!

Step Four: The Follow-Up

How do you know the date went well? Irene notes the signs should be obvious. “You will have amazing conversations. The time will fly by. You won’t want the date to end and you will be hugely eager to see the person again.”

Avoid the age-old misconception of waiting a week to text the person. “Be open and clear about wanting to see the other person again,” advises Irene. “Text or, even better, call the next day and make plans to meet up again sometime soon. Don’t hesitate and don’t play games. Seize this exciting opportunity!” And remember: the other person also wants this date to work out. Everyone, including them, is rooting for you. 

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