The first time I took my girlfriend out to a romantic dinner, it was reasonably priced. The next time I took her, the price had risen by roughly $10. The third time I thought about taking her to dinner, the price had risen yet again. Is this an intentional feature – and if so, could you explain it – or is it a bug?
I’ve run into this, and as far as I can tell the price increased according to my character’s salary. Did you get any promotions between the dinners that raised your base salary? When I went from a sous-chef to a TV chef, the price of the meals and movies nearly doubled…because my salary went up by a very good amount.
But, I’ve never been to a restaurant with a sliding scale! The game assumes that I’m taking my girlfriend to more expensive places, now that I earn more money? Heck, I usually go out for pizza, which costs all of $10 – I guess I’m not romantic enough. 
This is deliberate 
The reasoning behind it is part real-world (maybe I know too many materialistic people?) and part gameplay:
Gameplay:
We can’t make a romantic meal a set fee, because if the player gets a decent job, the cost becomes trivial, and the gameplay balance tips massively easier as you become better off. there’s no level it can be set at that isn’t unfair in some way
Real World:
If Bill gates took you out for a meal, would you feel happy about it being Burger King? I suspect not, but if your minimum wage boyfriend suggests a meal at a relatively cheap place, you wouldn’t mind. This is what the sliding scale is representing.
It does scale with your salary. Ideally there would be a dozen different romantic options and the partner would react by comparing the value of the expenses against your wealth, like they do with the romantic gifts. of course, that involves a dozen times as much work on the same area, which is why it wasn’t doable.
What about an option like restaurants? Cheap, Average, Expensive all done relative to the salary?
I think this is pretty cynical. It’s easy to buy someone stuff; look at Valentine’s Day. Any guy can go to a florist’s and buy a dozen roses but it is so forced because you’re supposed to buy stuff. Personally I’d rather have my partner do something that shows they care. I’d rather find out what her favorite tv show is and buy her the dvd edition because it shows I did it for her because her happiness is important. I’d dump a woman who expected an expensive restaurant just because I’m Bill Gates because she’s clearly more interested in my money than my personality.
This is also bad for other reasons. I was once able to take my lover out for 21 dollars on a romance movie. Now It’s 40 dollars because I got a different job with an extremely tiny difference in pay. The result? Instead of being a Laywer, I went back to my Waiter career because things were cheaper, and I could walk instead of taking the expensive bus.
I ran into this too. I quit my tv chief job and took a assistant chief job I could bike to. Lowering expectations was fun.
I did this for my wife who is celebrating her birthday this weekend. Shhhh…don’t tell her. 
Maybe a cool solution would be to have a solo activity where you spend an evening looking for an appropriate gift, which just takes up time?
I think the solo activity would be along the lines of the “Go Shopping” activity, and it should net you a gift that results in the same relationship boon as a “romantic” gift would, however it should be more stressful, or have some other con(s). I can’t think of any cheap yet equally appropriate gifts I ever got ma lady that didn’t require me travelling half-way across the country and sending me store to store in search of that very specific something.
This could be in-and-of-itself another gambling game where the quality of the gift would tie into the chance of finding that gift, with success of finding the gift giving a large relationship bonus but failure leaving you miserable, tired and wasting an evening. Perhaps relaxation and energy would drop but happiness and excitement increase…
Perhaps I’m looking too far into this
Wayno, an overweight and grubby waiter
i had a “movie date” in this game that cost 92 bucks…a 92 dollar movie?? Most of the time I just don’t bother with romantic relationships because im too cheap to fork over 92 bucks for a movie. I dont care how good the movie is! LOL
Please, I rather spend that 92 dollars by getting my date drunk. It’s much cheaper and would probably boost relationship scores up higher!
I think a similar question would be, as a female gamer who has thus far always made a female char for Kudos, what’s with always going dutch?
I’ve played several games all the way through, and not once has a boyfriend offered to take me out and/or offered to pay. 
I wonder if there also couldn’t be a way to have a “romantic dinner in” using the dinner party set up (especially if your char is a chef, why would they pay $300 to eat someone’s else’s food?) or a “movie night in” using the video games activity set up as a way to counter costs and add dating activities.