Ah, the good old days. I love a SD-SB relationship. As long as you are both singing from the same hymn sheet. I have my profile up on several sites, and straight off the bat, it is not unusual to chat for a bit, skype, then arrange a meet, where he covers the costs of travel, which will include some serious shopping, nice hotel, and then shag him senseless. As to items purchased, get a gift receipt if you can.
You are a riot, Violette!
Typically, with a Sugardaddy, you DON'T approach them. That's because I use SeekingArrangement and Sugardaddy for Me for civvie dating. The most successful SD/SB relationships happen when you don't come off so needy. Plus, nowadays the 'damsel in distress' bit gets very old QUICK. Great clothes and accessories, stylist-done hair, a nice flat, and for those in the US, a great car ALWAYS lets a man know he has to come off the checkbook. (You don't have to have it ALL, but any combination of these assets will work.)
Of course, so does being just young and hot too, but it ends up being more of a mind-fuck than anything if you're 'not singing from the same hymn sheet' (THAT is hilarious). Most men's idea of Benefactor is code for DADDY, which means 'I tell you what to do and when to do it.' When he feels like you have no life or no choice than to deal with him, he will offer to put you up in a flat, with a car and allowance, all so he can come by when he wants. So no friends, no plans, cause you have to be ready when he is. Too bad it's your mum's birthday, cause you can't go. And if you make plans when they make plans, they're like spoiled brats. Things with a guy looking for vulnerability always ends up bad.
As far as the arrangement is concerned, he will usually tell you what he is able to do for whatever level of involvement. If he doesn't mention it, tell him that you'll need a cash allowance directed to your bank account. Those who really know the deal and know they don't have the time for a LTR will anyway (your profile should say what you're open to, whether that's a LTR or NSA friendship.). Honestly anything you gain from a Sugardaddy relationship is meant to help your life, not to stop your life. I would not stop being an escort at all for a man unless you were about to be married. Even then it should be a gateway to following your dreams of making money in other ways.
But when you SEEM already financially set, it allows you to set the pace. He has to woo you. He looks at you and knows your inbox on Seeking Arrangement is full and there is competition for him. When my friend found a suitor on Sugardaddy for Me, she borrowed my clothes, my car, a condo that I used as my incall location, and now she's about to get married. After a month of dating, he wanted her to go on a month-long vacation with him, so she just told him to transfer the amount of her bills for two months into her account while he was at it. It was more than fair. She has a good head on her shoulders, and all she needed to show him was that she wasn't some lowlife gold digger.
All the best to you Sugarbabies,
Tiffani