2 weeks ago
First Date Tips for SDs: How To Really Charm a Sugar Baby!

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Even in the Sugar Bowl, a first date can produce some nerves for even the most confident gentleman. You might be asking yourself if your POT is going to be as enjoyable to spend time with in-person as they are online. Maybe you haven’t dated in a while and are a little rusty when it comes to the usual conventions. Or you could be a freshly-minted Sugar Daddy and unsure of how all of this compares and contrasts to traditional dating.

Whatever your situation is, it’s always a good thing to be prepared! Read on for some quick first date tips that’ll have you primed for Sugar success!

Going to Dinner? Do Your Research!

Chances are you’ve likely had enough conversation with your POT SB to know what her tastes are—the restaurants she frequents, the neighborhoods she likes to spend time in and what her likes and dislikes say about her personality or vibe. Use all of this to your advantage and pick a spot that she’ll enjoy and be comfortable at.

Along with that, do some preliminary research on your restaurant of choice to be sure it’s a suitable place to meet someone new. Avoid loud dining rooms—ones with excessive seating or those that have display kitchens—as they aren’t conducive to the conversation you should be having.

And as you’re meeting a Sugar Baby, make sure it’s impressive! It doesn’t have to be five-star (let alone a Michelin three-star), but any fine-dining establishment will do. Sugar Babies don’t want you to take them to the Cheesecake Factory, SDs—but you probably already knew that!

If possible, try finding a place that checks off all the previous requirements and is somewhere you’ve already been. This allows you to suggest a particular cocktail or dish that you previously enjoyed.

Arrive Early—Punctuality is Important!

Sure, you’re a successful businessman and a lot of your time is likely tied up. But you’re looking to date up—and you should never leave a beautiful woman waiting. Consider scheduling in 15 minutes of leeway time in case you get caught up at the office or traffic is worse than usual.

Not only is this polite, it also offers a couple of advantages if you arrive with time to spare. If you’re going out for dinner or a round of cocktails, the extra time allows you to scan a cocktail menu or speak to a bartender or waiter to have some suggestions ready when she arrives. And if you’re seated first, you can greet her in a chivalrous way by pulling her chair out when the host or hostess escorts her to your table.

Be Charming—First Impressions Matter!

While first dates should in no way feel like a job interview or potential client meeting, there is one major similarity: You always want to present your best self. Just as you’d act in a more refined manner when meeting potential new business partners, you should do the same with your potential Sugar Baby.

So, have a humble confidence about you, observe proper etiquette and, if you’re out for dinner or drinks, be kind to the wait staff. Also, consider keeping curse words to a minimum for this first meet—you’re not at a sports bar talking trash with your drinking buddies. You’re trying to charm an attractive woman and enjoy your time with her—why not be charming then?!

Be a Good Listener

Especially on a first date, a conversation should be back-and-forth, give-and-take. Commanding the conversation with your personal stories is likely going to bore your POT after some time, so consider instead being an active listener and take an interest in what she has to say.

Now, that doesn’t mean simply waiting for your turn to speak and asking another question. Really hear what she’s saying and remember a detail that you find intriguing—when you’re both interested in the subject at hand, a natural banter will flow effortlessly.

Boast in Moderation

You’ve worked hard for your success and yes, the Sugar Baby you’re meeting finds that quite attractive. What isn’t attractive to SBs is excessive name-dropping and making the time you’re spending with her all about yourself. As previously mentioned, make sure the conversation is flowing—keeping your humble (or not-so-humble) brags to a minimum is a great way to make sure that happens.

Sure, if dropping a name or throwing in a detail that’s impressive is natural to your conversation, by all means go for it! Is she a New England Patriots fan? Tell her about the time you partied with Rob Gronkowski. Are you discussing recent vacations? It’s a perfect time to tell her about the adventures on your yacht in Miami. Did your POT spend a semester in Paris when she was going to college? This is the time to tell her about the summer you spent in the south of France.

Touching Should Be Natural

This is your first meeting and showing interest is definitely something to consider doing—and subtle touching is a great way to be flirtatious, whether it’s putting your hand on hers on the table or touching her shoulders after you push her chair in.

However, too much hands-on flirting might send the wrong message to your Sugar Baby. If you do a lot of this on the first meeting, she might think you do this to all your first dates—and that’s not exactly making a woman feel special. It also might give her other unsavory impressions of what your intentions are. So, let this come naturally and don’t force it.

Having the Arrangement Talk

If you’re really hitting it off with your potential Sugar Baby, the discussion about an arrangement might come up. There’s no pressure or no need to bring this up on the first meet, but you certainly can do so if you feel the moment is right.

Just in case the conversation leads in this direction, have in mind what your terms and expectations for the Sugar Relationship will be. Chances are your POT also has considered this potential discussion and is also ready with that exact same information.

Walk Her To Her Car, Subway Stop, Etc.

While many like to joke how chivalry is dead, there are still many women out there who are looking for a gentleman to sweep them off their feet—and Sugar Babies are no exception! Walking your POT to her mode of transportation is a classy move to take at the end of your date, as it shows you care for her safety and also expresses interest. You wouldn’t want to continue the conversation if you weren’t hoping for a second date and/or arrangement, right?

Have a Good First Date? Let Them Know!

If you enjoyed your time with your POT Sugar Baby, follow up by sending them a text message (or message on Seeking) that night or the next day to let them know you enjoyed your time with them. This is not desperate; it’s courteous.

Plus, Sugar Relationships are about open and honest communication. No one in the Sugar Bowl is playing games!

So, do you have your own first date tips for Sugar Daddies? Let us know in the comments on the Facebook post about this blog!


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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