First Date (GTA IV)
This is your first date with your new girlfriend Michelle. Before the cutscene begins, a tutorial is given on relationships, which shows how different friends and girlfriends have different likes and dislikes, and each friend will offer a different reward for maintaining a good relationship.
The Actual Date
You can't go on the date itself until you get some new threads- see the Bonus Advice in "Easy Fare" for elaboration on that. So go get a hat or something, then drive over to Michelle's and ring her up. Note that while you can ring her up on this from just about anywhere in the city, it's a good idea to do so only after you're near her house, since if you take more than an hour to get there you'll have stood her up, and her disposition towards you will take a hit. Calling her to inform her you can't make it before the hour is up will soften the hit, but it's best to just wait right nearby so you can roll right onto the mission marker.
At any rate. Hit up the mission marker and watch the cutscene to get a preemptive hint on your next destination- you may have already noticed the "funfair" while driving around in Hove Beach. Follow your GPS to the spot, only to find (from Michelle) that Firefly Island is closed this time of year (the dialogue may vary). Michelle suggests the bowling alley nearby as a viable alternative, and it's good advice. Walk there now, then sign up for a game. Any empty lane will serve.
Play five frames of Bowling (the game should give you advice on how to play, and it becomes decently intuitive after a little while), then head back to the car and drive Michelle home.
RE: Bonus Advice
A few things. First off, as regards the Bonus Advice in "Easy Fare", getting only one item of clothing at first is a good idea. Michelle has a particular favorite outfit she likes for you, but this varies from game to game. Getting only one new item at the start and then switching it up will work wonders, as on every subsequent date she will note what she likes or dislikes about your outfit. Use this advice to compile a "favorite outfit" for her (Not necessary, but every little bump helps).
All girlfriends and guy friends have certain things they like or dislike to do. Girls tend towards comedy, cabaret, restaurants, and sports (E.G. Split Sides Comedy in Alongquin, Perestroika in Broker, and all the pool/darts/bowling things). Guys tend to like sports, drinking, and always, ALWAYS, the strip clubs. While it's usually a bad idea to take a girl to the game's two strip clubs for a date, this approach will work wonders with friend dispositions- two or three trips should get you 100% and their perk. Michelle isn't particular about anything, so use your dates with her to familiarize yourself with the city's nightlife.
Finally, Michelle herself. Getting her to 100% disposition doesn't earn any perks like with other girl or guy friends, making it not really necessary to do so unless you're going for the 100% completion, but she is the easiest to get to like you and hence the easiest track to the "Warm Coffee" achievement (if you're playing this on the 360). Note that you must do this before the "Snow Storm" mission later on in the game- that may seem far off right now, but it'll come at you like a freight train, so work on getting Michelle on your good side while you can. Also, note that she has some rather odd pillow talk- you'll see where that comes from later.