What to Expect on Your First Sugar Date

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It’s time for your first sugar date, you’ve been chatting with your sugar daddy online, and now it’s time to have your first face-to-face rendezvous.

Meeting a sugar daddy in person can be an exciting and fun prospect, really something new to look forward too, regardless of the thrill involved, initially it can be daunting and quite scary.

You can never be too prepared and it would be wise to chat with other sugar boys about their first sugar date experiences. To save you some time, I’ve put together a few points on the most common things you have to expect from your first date.

Safety First

Before getting all dressed up and actually going, you have to do a background check. Ever heard of catfishing? Is the sugar daddy really who he says he is or have you been talking to a fake profile?

Always suggest meeting somewhere public or where there are a lot of other people around. Not only will this make you feel more comfortable but also safer.


Trust your intuition, if something feels off, it usually is. Remember your first date is to ensure that the two of you have a real connection to decide whether you want to continue the relationship or not.

Being open-minded, friendly and charming will help make both of you feel at ease.

There will only be a few awkward minutes of silence if you don’t take the initiative to start an interesting conversation. Sugar daddies enjoy sugar boys who can carry a conversation (not take it over).

You know many things about your sugar daddy already, whether he likes technology, is into stock trading or fishing. Ask him questions about these topics and show genuine interest.

First Impressions Count

Yes, your conversation is going to reel him in. Before he listens to your mind he is going to see you. And being a sugar boy you need to look the part. Spend time on grooming and dress to impress.

Your Sugar Daddy will be checking you out, so make sure you give him something to look at. Smell good and get a haircut.

Analyzing Each Other

Be sure that the two of you will definitely be sizing each other up. Analyzing body language, speech, and other nervous twitches. It’s important that you stay calm and poised and most importantly just be yourself.

Most Sugar Daddies don’t look like the Wolf of Wallstreet but they are experienced and they talk the talk just like they walk the walk. Avoid looking at his watch and shoes to see who he is, he may be filthy rich without the glitz and glam appearance.

If he treats you to dinner, show him that you are grateful that he paid, if he sees that you appreciate small things like dinner, then he’ll know you’ll be appreciative of the Sugar Relationship arrangements.


Honesty is key at your first Sugar date. Be open if you feel a bit nervous, he will find your innocence even more attractive. Feel free to ask him questions about the procedure (leaving money talk out of it, for now).

Try to compose yourself and be at ease, but don’t pretend to be someone you are not. You don’t want to be dishonest on the first day, pretending to be something you are not, just to surprise him with the ‘real you’ later on, is not a good idea.

It Could Turn Out To Be Disappointing

There’s a big difference between having a connection through online messaging and actually having a connection in person. Be prepared that you might be disappointed with the outcome of your first encounter.

If you are disappointed by the subtle hints that may look like he isn’t interested in pursuing a relationship with you, then try to enjoy the rest of the evening. Being rejected is part of the game. It’s how you deal with rejection and disappointment that makes the difference.

While a first Sugar Date can be a bit stressful, you should try and stay in the moment and enjoy it. If you’re going to spend more time with your Sugar Daddy in the future you should be able to let go and have fun.

In the end, that’s what it’s all about.

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