Lately I've started to find dating in sims 2 really monotonous. If I just follow the wants, then it always ends up the same and feels really repetitive and boring. Talk/Entertain>Flirt>Makeout>Woohoo (if possible)... Yawn. The problem is if I try to do anything else (even dining!!) the date meter slows down too much and I risk it ending too soon. What do you do to make dates more fun?

I'd be interested to hear what other people say, because this is something I've been struggling with myself.

Lately, I've settled on a kind of strategy. First, before I have someone ask for a date, I decide what kind of date is it. There are three basic kinds: a getting-to-know-you date, an I-really-want-to-woohoo date, and an I-want-to-get serious date. For the first type, they have a coffee together or lunch and chat, and it's usually okay if the dates are short. For the second, just follow the wants and see how far they get, then end the date once they get to woohoo or get up to dream date. The third, they go somewhere nice, do some romantic wants to get the meter up, have a nice dinner, try to get up to great or dream date, and then pop the question if everyone seems amenable. I also sometimes have them have bad dates, such as if they are on a date with one Sim but rolling wants about someone else, so I figure they are distracted and not focusing on their date or they really want to be with that other person instead. My sims who are coupled rarely go on dates, unless maybe I want to do an anniversary scenario or they are trying to rekindle the romance. I think that if they just want to have a fun time out together bowling or something, it's better to have them go on a casual outing instead of a date.

Depends if the date is on a community lot or at home. Personally I think "get to know you" dates are challenging enough on their own as you may not be able to fulfill some of the wants your sims roll or they may get rejected. The one thing I don't do on them is to use the ACR functions as the parameters for acceptance for those interactions are so much lower it feels a bit cheaty to me.
Let's assume this is for sims already in love/engaged/married then.

For just a regular date on a community lot, I try to get that first time bump as quickly as possible so that I have a block of time. It's usually a combination of gossip, telling jokes, tickling, back rubs, and dancing. Once I get the extra time then I go for dining during which they may flirt, play, entertain, and so on. Really depends on how much they talk and how slow they eat. If there is a neat sim I keep the extra's to a minimum cause I don't want the meal to last forever.

After the meal, if I haven't hit the next time bump I will shoot for that depending on what want they have. Then they may bowl, play pool, dance, sing karaoke, heck I've even had some of them play chess together. Depending on the age range and where they are in their relationship they may just go back to the playable sims home and continue the date there.

It might sound a bit formulaic and up to a point, it is because you have to gain that extra time in order to really do much. I do tailor the dates to the individual sims though. If I have a super shy and serious sim I'm not sending them out to a nightclub and expecting them to dance and woohoo in a photo booth for points. Likewise, if it's an outgoing and playful sim I don't ask them to settle for a quiet meal at home followed by a bit of cuddling on the sofa.

While you do have to pay attension to the wants -if you want a good date (getting a bad date can be fun too) you don't have to jump to it's every wish. The date doesn't have to be a dream date and they don't have to woohoo. Like sturlington I do different kind of dates. A getting to know you date can be more about the sims personality. Do enough of the wants to reach good, while making the rest of the date more about what you think these sims would want to do if they wern't chained to the Maxis want system. Movies, fishing, art museum? Maybe they are a pair of nerds who just want to play chess and take things slow.
If it's a married couple trying to sneak in sometime before a baby or toddler needs them maybe it will be a few kisses and a wohoo. It's a about ballance as you don't most times want a terrible date but don't worry too much about the meter and the wants unless time is running out and you want to extend the date.

I play dates based on the level of niceness/grouchiness of the sim asking out.
If grouchiness is <5, the sim will mostly fulfil his/her wants and if s/he's nice >7 then the wants of the date will be fulfilled first.
If niceness is 5 or 6, the sim will fulfil the wants s/he wants to.

Also consider whether sometimes what you want might be an outing rather than a date. You can still think of it as a date, if it's an outing of only two people; but if what you want is for Nina and Don to have a night out bowling with no pressure, than an outing works better, mechanically, than a date.

Yes, ^ Untimed outings can be a great way to have two sims connected without the pressure of a meter. This game is one part mechanics and the other part only limited to your imagination.

Usually when date is already pretty good, I let them continue by themselves, It shows me what they really want to do. Recently at the middle of the date ACR decided to take it over. And I had disaster date too when my sim and her date decided to use hot tub and then lightning striked.

Hard agree on the untimed outing being a great option for a fun night out. I do use the dates though to up a low aspiration or for the possible dating gifts for a super poor sim. There really are endless ways to play this game. I'm a big fan of untimed outings to build social and reinforce social groups. When I really think about it I very seldom have a single sim out alone unless they are romance sims on the troll.