3 months ago
First Date Tips To Charm Like a Gentleman

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You perfected your profile. You filled it out with wit and personality, hoping your charm would emanate from the webpage. You had a professional photographer take your profile photos. You’ve been focused, signing in daily and searching for potential matches—and being discerning when you had to, of course.

You’ve made all the right moves—and then some—and now you’re here: The first date! But, the thing is, the impressing isn’t over! A first impression happens only once, so you need to dazzle on this date—without going too over-the-top, though.

While many like to think that the latest wave of feminism cut the life support from classic chivalry, it actually is not dead! Being considerate, having good manners and showing respect are all still qualities that many look for in their partner—go figure! Don’t worry, no one expects coat-over-puddle chivalry anymore—your Armani suit jackets are safe!—but a little courtesy can really go a long way on a first date.

Sure, your dates are already impressed by your wealth and success—you’re elite dating, after all—and they likely look forward to getting to know you. But why not really wow them and leave them anticipating your next date (or the possibility of a long-term arrangement)?

Whether it’s been a while since your first date or you just went on one last night, there’s always room for improvement! Here are a few tips that’ll have you shining like a true gentleman on that next first date.


Pick The Right (Refined) Location

The devil is in the details, right? You’re elite dating now, and where you decide to go on the first date is going to say a lot about you! It’ll tell your date something about your personality and how you live your life.

It likely can go without being said to immediately exclude any fast-food situation from your options. But, just in case there’s a Salt Daddy or Splenda Daddy out there reading this, do not take your date to Chipotle—or any place where you have to scream your order over a plastic partition, really.

Now, elite daters aren’t always expecting to be wined and dined at a Michelin-starred restaurant—though no one is going to fault you for taking them to a Thomas Keller or Joël Robuchon joint! But taking your date someplace special—whether it’s a restaurant, a cocktail bar or elsewhere—is what’s important. Consider what your date would like to do but make these plans on your own—keep the element of surprise!

Do you have connections at a restaurant known for its difficulty to snag a reservation? Use it! Did you just find out about a new café that’s blowing up your city’s dining scene? Check it out! Or, maybe your date has an affinity for craft cocktails—take them to your city’s top cocktail bar. Is there a music festival in town? Go together. Going somewhere special turns a first date into an experience—something special that your date is going to remember.

If your city’s dining and entertainment options aren’t available date destinations due to pandemic restrictions, get as close to the real thing as possible. Order takeout from your favorite fine-dining restaurant and spark some candles for a candlelit dinner either at home or in your hotel room. Stock a wet bar with your favorite top-shelf spirits, mixers and garnishes and play bartender from your own kitchen. There are all kinds of ways to make things work social-distance style—you just have to get a little creative!

Be Present—Don’t Think About What’s Next

For many, it’s how the date ends that’s most important—it’s whether they get a first kiss, get another date or get intimate. But if all you’re thinking about is what might happen next, you’re going to miss out on what’s happening in the moment.

Go into your first date with no expectations and let things play out naturally. Get to know your date better and think about where you’d like this meeting to go—specifically, is your date going well? As for an arrangement, talk about it when it feels right—and that might be over messaging the next day; it’s all up to you.

If your date brings an arrangement up, feel free to discuss it if you’re ready and willing to—or suggest finishing your date and discussing the arrangement later. It’s perfectly polite to respond with something like “Let’s talk about that after dinner; right now I want to get to know more about you.”

Simply enjoy your date’s company. As for how to do that? Take a look at their profile one more time before your date so you can ask them about what they’ve listed—their hobbies and interests, where they’re from, their favorite sports teams, etc. Try to avoid talking about work or your job and name-drop/boast about something when it’s natural to do so.

If the date is successful, move forward with your relationship how you see fit! But if the date isn’t so successful, simply let the person know you enjoyed meeting them and don’t offer any promises for messages or phone calls that you don’t plan to follow through with. There are plenty of elite daters to meet, but not all pairings are a match!

Don’t Show Up Empty-Handed

Go for the cliché and show up with a bouquet of flowers for your date. It’s borderline cutesy/romantic and will put a smile on their face right away. Who doesn’t want to kick the first date off right? This is a surefire way to do just that.

You could go above and beyond with some gourmet chocolates or some kind of gift, as well. This is elite dating and the sky is your limit. But the flowers are an old-fashioned charmer. They’re unexpected and your date will appreciate the chivalrous gesture.

You could go even a step further and do some simple investigation work by asking your date their favorite flower beforehand—stealthily, of course. Try working it into conversation if you can. Try giving their Instagram a look to see if they’ve posted any flowers, or take a peek at their SeekingArrangement profile to see if they’ve mentioned it anywhere—maybe they even have flowers on their SA Wishlist.


This is by no means a comprehensive list of what will guarantee you a slam-dunk first date. A lot of how your first date goes obviously is situational.

However, remembering these tips might just improve your game next time you’re out with someone new. Enjoying an experience, living in the moment and being a true gentleman isn’t going to hurt your chances at a second date!


Enjoying all the Sugar Dating stories, advice and tips, and curious about jumping into the Sugar Bowl yourself? Create a FREE profile on SeekingArrangement today and start experiencing the advantages of empowered dating and mutually beneficial relationships!

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