Obviously to start out with you have coffee, drinks at a nice/fancy bar, lunch/dinner.
Once you start to get closer and more intimate, dates I have had or am planning for the future are:
- wine tasting at a vineyard, or tasting scotch at a distillery, or beer in a brewery
- for bars, take him to a secret speakeasy he doesn’t know about, or suggest he gets a room at a luxury hotel with drinks in the bar beforehand 😉
- couple’s spa/ massages, champagne and plenty of private time
-if your SD likes clubbing, invite your hot girlfriends (make sure you can trust them not to steal him away) and have him get a table at an exclusive club.
-have him take you to Vegas to gamble! He should give you some money to play with, and maybe you can win some more to take home
- shopping at boutiques/department stores (pick things out for him too! Make sure it’s not just all about you. Choose things you think look good on him and tell him he looks sexy, that way he’s less likely to feel like you’re using him.. though of course you are)
Also, you can ask him to pick out clothes that he thinks look good on you (or lingerie 😉) that way, you can play it off as him buying you new clothes for his own enjoyment! Tell him “I can’t wait to wear this for you..”
- if you’re not shy, take him to a sex toy shop.
- have him take you to a concert or play in the VIP section.. maybe you want to see Jay Z, Beyoncé or Kanye on tour? Or maybe he enjoys Broadway?
- for the more refined SD maybe ballet or the opera.. if anything it’s a nice excuse to get dressed up in black tie and look stunning. If you don’t know anything about it read up on whichever show you’re going to and the careers of the performers, and make it sound like you know what you’re talking about!
- for the sporty SB’s go skiing, play tennis or even better, golfing. If you know how to golf that is a huge plus in the SD world because it’s a sport that many businessmen enjoy and use to close deals! Use going golfing with him to close your deal 😉
- if you don’t want to play a sport then you can at least go to a game with him! What’s his favorite sport? Football, soccer, baseball, basketball? Maybe he can get court side seats! And again, read up on the sport so you’re not constantly asking him to explain what’s going on. Nothing is more annoying. You don’t have to go overboard and pretend you’re a huge fan, as that’s annoying too if you’re faking it, but at least have a general idea of how things work.
- upper class sporting events include polo (veuve clicquot polo classic for example), Wimbledon or the US Open, or the Masters golf tournament. These tickets are generally more expensive, and you should dress nicer.
- cooking classes! Learn how to cook each other’s favorite meals
- gallery openings and museum exhibitions, or charity galas. This depends on whether your SD wants to introduce you to his friends and society (assuming he is part of society). Even if he isn’t, you can buy tickets to major art events such as Art Basel in Miami. Or attend an art auction by major auctions houses such as Christie’s or Sotheby’s
- Getaway for the weekend to the beach! Remember, if he’s kind enough to book tickets and arrange everything, it’s your job to make the weekend as stress free and relaxing for him as possible. And long walks on the beach, while cliched, are still very romantic! And take care of him while you’re there - for example make sure his drink is always full (you order with the waiter so he doesn’t have to) and put sunscreen on him, throwing in a little massage.
- My SD took me in a helicopter to the Hamptons. Got to see this incredible view of New York as we were flying out (and on the way back as well)! Or for the more adventurous pairs.. sky diving?
- have him rent a yacht for just the two of you for the day/weekend (or if he owns a yacht, even better)!
- for the traveling SD, have him take you along on his business trips. London seems to be a common destination for these types, as does NYC, LA, and Hong Kong.
- take a short weekend road trip if you can’t travel for longer. For example, go to Nantucket from Boston for the weekend, or drive to Napa if you live in California
- stay up all night kissing and talking until the sunrise is a sure fire way to make him fall in love with you and have him wrapped around your little finger
- more couple vacation ideas include going glamping on safari in Africa (not like camping at all - it’s like a five star hotel with air conditioning etc that just happens to be in a tent rather than a building), going salsa dancing in South America, scuba diving in the Maldives or Fiji, or shopping in the souks in Marrakech!
- you can always surprise him by showing up at his door with movies, a bottle of wine, and wearing a coat with nothing underneath!
You can really make memories to last a lifetime with your SD footing the bill, and it’s a win win for all as he gets to go on dates/vacations with a pretty young thing and make memories as well!
And remember, it’s his experience as well, especially since he’s paying for it. You should be low maintenance and non fussy - to an extent. Obviously your plane tickets should be first or business class, but don’t kick up a fuss if he takes you to Italian instead of Sushi, for example. ALWAYS, ALWAYS BE GRACIOUS AND GRATEFUL!!! if he wanted someone nagging him and being bitter/bitchy/passive aggressive about stupid details, he’d get a girlfriend or a wife!
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