Let’s meet for a cup of coffee
Meeting for a cup of coffee is too informal non-committal. He can set up a meeting at Starbucks and be done with it after just 20 minutes and a $3.95 latte. He can nearly have his first meeting while double-parked.
He is not investing enough in the meeting.
Let’s have drinks
That can be a good option for you. Pick a nice, upscale place where they have good bar in a restaurant or where there is a great restaurant in the same building. Then pick 6…7pm as the starting time.
What is great about meeting for drinks is that there is a bit of commitment on it: He will have to park somewhere because you wouldn’t suggest (and he wouldn’t either) a place right next to where he lives or to his office, he will be buying drinks and that will me much more expensive than a coffee, and meeting for drinks there is an expectation that your date will take longer.
You want enough time to make a connection, start some meaningful conversation, and show your charm and personality. Having some drinks will help both of you relax and enjoy the moment. However, if he is not someone you want to move forward with, it will not be difficult to finish the date in less than one hour and excuse yourself.
And oftentimes a good drinking date will turn into a dinner date, especially if the restaurant is right next door and it is dinner time!
Let’s have dinner
There are many ways to set up a first meeting, but in our experience the dinner date is the most convenient and advantageous set up for you, the sugar babe. It has all the advantages of a drinking date plus you will have more time together and if you were to choose not to spend time with him you could always end the date while you were still at the just drinks stage. You will also have the opportunity for better positioning: Don’t sit across the table from him, sit beside him or in a 45 degree angle.
You will also have a better opportunity to evaluate his choices of food and wine, his manners, and the way he treats the waitress and other staff. If he is rude or condescending towards them it is certain he will be rude and condescending towards you given enough time and/or alcohol.
He will also have enough time to get a better impression of you, to watch as you walk towards the bathroom once or twice, enough time for chemistry to happen… or not.
Let’s meet at my place
Very bad idea for a first meet. He will be in his territory and you will be under enormous pressure. It is dangerous, it signals that you don’t have good judgement, and tilts the odds towards one-night-stands, which is all you deserve if you read this article and still make this wrong choice.
Just as bad going anywhere else if he will be the one driving and you don’t have the money to pay your own cab to go back home. You will be trapped. If you live in Boston and he invites you for a first date at Foxwoods (2 hours away driving fast), you are in for a high-pressure date.
Also keep in mind that he will have to do the driving after having drinks, and if he was eager to have sex with you and that is not what is going to happen you will be driving back with a drunk and grumpy man. Not your idea of a good time, I bet.
Let’s go to a nightclub
Another bad idea. Don’t choose any place where the music is loud, you can’t hear each other, and there will be many distractions. Also any place where the interaction is not between the two of you, like movie theaters, concerts, or shows.
Let’s go to your place
Another very bad idea!
Surprised? Seems good in principle because you will be in your own territory, don’t need to drive anywhere, and if you want to shag this cool cat what would be more convenient than you own place, right?
Well, all that is right. The problem is that you don’t know for sure if you are going to like him. And if you don’t like him and he likes you, if he is a lonely fellow, or he doesn’t have a pretty good grasp of reality, now you have a stalker right in your living room. Worse than that: A stalker that knows where you live.
Don’t bring your sugar daddy to your home any sooner than you would bring a new boyfriend to your home.