The First Date: 10 Tips to Help You Master the Art of the Sugar Date

You’ve been busy. You’ve been emailing and chatting with potential sugar daddies galore. You’ve weeded out the undesirables. And you’ve emerged with a handful of potential sugar daddies you want to meet.

Congrats! Now we’ve come to the fun part: the Sugar Date.

The first sugar date is of monumental importance. Why? Simply because it is the point that marks the beginning – or end – of any potential sugar relationship.

Most sugar daddies will know whether they want to enter into an arrangement with you after this one date. Most sugar babies will know whether they want to proceed with the arrangement after this date.

It’s the date that makes or breaks a potential sugar relationship.

That might sound like a lot of pressure, but it’s really not. It’s a great opportunity to strut your sugar game, instantly find out who you’re compatible with (and cross out those you’re not), and be treated to a fabulous dinner – all at the same time.

To ensure your first sugar date is awesome, here are some tips we’ve compiled from our own experiences as well as those from other sugar babies.

If you have more to add – pitch in in the comments!

If you’re still not feeling totally confident about your ability to woo a sugar daddy on the first date – we really recommend you try out What’s Your Price. This site lets generous members bid for a date with you so you’ll be able to get paid to go on first dates and practice your A-game. It’s also totally free for you to join 🙂

First Sugar Date Tip #1. Fun First

The first sugar date is crucial. He’ll size you up. You’ll size him up. And you’ll both come to a decision as to whether you want an arrangement with each other.

There’s a lot going on. But that’s no reason not to have fun.

In fact, your most important priority on a first sugar date is to have fun. After all – what’s the worst that’s going to happen? He’ll decide you’re not what he’s looking for? So what? – you get a chance to try out your sugar baby charm on him while being wined and dined.

Just concentrate on having fun – that is the best impression you can make. And if it doesn’t “work out” – hey, at least you had a fantastic time.

First Sugar Date Tip #2. Know Your Stuff on His Stuff

Conversation is crucial to a successful sugar relationship. Most sugar daddies tend to appreciate sugar babies they can have good conversations with.

Brush up on your potential sugar daddy’s interests before meeting. From your emails and chats, you’ll already know what they’re into – are they history buffs? Crazy about technology? Love traveling?

Use what you know about them to get to know more before the first date. You don’t have to be an expert in anything they’re interested in – just get a general understanding so you can be an interested and attentive listener as well as ask relevant questions to keep the conversation flowing.

First Sugar Date Tip #3. Stay Safe

The first sugar date should always be at a public place. If you can – make it a place of your choice, somewhere you feel comfortable.

This should be easy since a sugar daddy will most likely let you choose the restaurant or recommend a few for you to choose from. If he doesn’t, suggest it with a “I’ve been dying to go to ___. Want to meet there?”

If he offers to pick you up, politely decline and ask for cab fare. Actually, even if he doesn’t offer to pick you up, you should ask for cab fare.

Check out more sugar baby safety tips!

First Sugar Date Tip #4. Dress to Impress

Some sugar daddies love eye-catching arm candy. But most are low-key and prefer understated elegance or casual classy to outright flashy.

Choose your outfit according to the potential sugar daddy’s preferences, if you already know them.

If you don’t – for first sugar dates, we love understated, well-put-together outfits with a hint of fun. For ideas, check out some first date sugar baby looks we love.

First Sugar Date Tip #5. Your Ease is His Ease

You might be suffering a case of nerves over the first date, but guess what? You’re probably not the only one.

Quite a few sugar daddies are nervous the first time meeting. He might be feeling self-conscious about the fact that you’re much younger than he is (and appear obviously so) or he might be downright intimidated because of your looks.

Your job is to make him feel at ease. And the easiest way to help him feel at ease is to be at ease yourself. People play off each other’s energies and your body language speaks volumes so take the time to relax yourself before meeting your potential sugar daddy.

First Sugar Date Tip #6. Old Friends Over Awkward Encounter

There is nothing more lethal to a first date – especially a first sugar date – than bland small talk.

Instead of pre-prepared questions, approach the potential sugar daddy as you would an old friend.

Greet him like you already know each other: “Hey! It’s awesome to see you! How was your day?”

And launch straight into normal conversation, just as you would with a friend: “So…tell me ’bout your day…anything exciting? I, for one, would love a glass of wine. Anything you recommend?”

Smile often. Laugh more often. Maintain eye contact. And keep the conversation flowing easily, naturally simply by expressing genuine interest in his day, his life, and his interests – just like you would with a friend.

First Sugar Date Tip #7. Sizing Them Up

A person’s appearance and demeanor speaks volumes about them. Take advantage of the first date to suss out whether this POT is sugar daddy material.

Observe not their wallet, their cufflinks, or their shoes, but their mannerisms, their eloquence, their overall conduct.

Many good sugar daddies may not look the part, but they will act it.

Does he ask you first what you want to eat? Is he interested in what you’re saying? Is he asking questions? How does he talk about his family, his employees, i.e. the people most important to him? Does he like taking care of them and knowing they’re happy? Is he nice to the waitstaff? How much is he tipping?

These little details matter. A lot. A sugar daddy who expresses interest in taking care of those important to him makes a great sugar daddy. A sugar daddy who cares that you’re happy with dinner is going to care that you’re happy in an arrangement.

Take note of the important details.

First Sugar Date Tip #8. Leave Money Out

One of the best first sugar date tips we can give is: leave the allowance talk for later.

Find out why here.

First Sugar Date Tip #9. Stay in the Moment, Stay Positive

There might be a lot of things running through your mind on your first sugar date. Am I dressed appropriately? Does he like me? How am I going to pay my tuition if he doesn’t? OMG…do I know those people at that table?

Whatever it is that’s on your mind, you can come back to it later. For the duration of the sugar date, the present is the only thing that matters.

The best way to guarantee a great first sugar date is to stay totally and completely in the moment. Show interest in your date. Appreciate the yummy foods you’re eating. Laugh about things happening around you. Relish how beautiful you feel.

Everything else can wait. Don’t bother yourself – or your potential sugar daddy – with pressing worries or concerns. Stay in the moment and share only what’s positive.

First Sugar Date Tip #10. If It’s Good Enough for Cinderella…

An hour or two is perfect for a first sugar date – even if it’s a leisurely dinner.

Even if you’ve had a fabulous time and the dynamic is amazing – avoid staying too long. He might want to keep you out longer, he might suggest all sorts of fun and inviting things to do, he might even offer a shopping trip.

But don’t be tempted – you’re after bigger, greater things. Whatever he suggests, politely decline and leave him wanting more.

A good sugar baby knows her time is precious. Don’t be giving it away before the arrangement is finalized.

15 thoughts on “The First Date: 10 Tips to Help You Master the Art of the Sugar Date”

  1. when asking for an allowance for example the girl in thr article below is that weekly allowance or monthly and how long do these arrangments last.

    i have a few questions so if anybody want to email me to answer my questions that will be a great help thank you everyone

  2. This may be a really dumb question, and if so, I apologize.
    How do you get cab fare/ let your potential SD pay for an Uber/etc before you meet him? Is it just generally expected that I pay for it and then he’ll reimburse me? Or do I just give him an address that isn’t my home for the cab pickup and dropoff?
    Thanks so much for your time and this fantastic website!

    • SD should be providing transportation. Your time is valuable, and it’s not uncommon for SD to offering uber/cab. However, if they don’t, it would be good to mention that travelling is a bit far for you and you aren’t comfortable just yet with them picking you up from your home. I always mention transportation, and a SD never fails to offer a means for me to get to the desired location. I always get the cab/uber to pick me up at the plaza around the corner from my house, as this is the safest way for the first few meet ups.

  3. I have a question. In tip 3 you suggest to ‘demand’ cabfare, but in tip 5 you say not to talk about money. Could you explain yourself more clearly?

    Thank you for the reply.

    Also: is it usual to have sex with a sugardaddy? And what is POR?

    Many thanks!

  4. Hi my name is Ladonna marie Williams is am 28 years-old I looking for great guy who is single who doesn’t cheat on me for anyone else he cannot be a sexoffender I don’t need to with a guy who sit there and lie he got to be single and don’t ki

  5. I want to ask about sharing information. Im from a very broken, problematic family,, being with him is so comfortable, so can I share wmtj him about problem at home? He ever asked tht I can share any problem with him.. Was it ever harm? Was it beneficial for me or it cost my allowance?

  6. What do you do when you know they are going to want to be intimate at some point in the future but you are not attracted to them at all…I am 36, but I sure don’t look like it, and I don’t feel it! I know I’m a bit older than most, and I don’t know if that is why, but I am getting very old men talking to me. But the idea of ever having to sleep with them puckers my you know what!!! What should I do? How do you get over that? Or do I just stick to what I find attractive and stay with that? I would really love some advice in this area….If you could email me personally that would be great!

  7. I’m a beginner and want some advise, i wanted to ask if it’s necessary to have an intimate connection on a first date? if it leads you to have sex already? and how to get over it if I’m on the actual scenario.. looking forward for your advice! btw the advise is really informative and useful thank you!

  8. And what exactly is wrong with being a gold digging whore? At least they are honest and everyone knows where they stand.

  9. I’ve never read an article more blatantly written by a broke man. Leave the money talk out of it for the first date ??? HAHAHA! That should already be established by the man before you even meet otherwise hes a splenda wasting your time. 😉

  10. Thank you for sharing this wonderful post on your site. It contains a lot of information and has answered every question I have in relation to the topic. I really appreciate it.


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