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@firni: I don't like that pressure either, to order an appetizer, entree, dessert, coffee. Many times I'll order a meal that doesn't include a side, and the server will sniff at me "Is that allllll? Are you sure you don't want a soup or salad?" I understand that busier upscale places don't want a small eater like me taking a table that isn't going to make them much money, but I don't usually dine in places like that! (and my usual dining companion more than makes up for my small appetite, haha.)

That being said, I don't mind a long menu, as long as it's clearly presented. "Creatively" named sections, tiny fonts, and pompous terminology make it hard to decide in under 10 minutes.

I have to agree with conky: "Suggesting a chain on a first date sends me a message that he's just not that into serious eating"... I live in a city where there are tons of excellent non-chain options. I wouldn't really consider a chain a deal-breaker, I do sometimes like a good burger -- I'm not "above" hitting a chain once in a while. I think my issue with the chain on a first date is that it's not really intimate or memorable, you know? Sitting in a booth at Applebees with the music blasting and a bunch of kitschy crap hanging on the wall doesn't put me in a romantic mood.

Although I also hate when a guy picks a really upscale, overtly "ROMANTIC" place too -- most of the time they insist on paying, so you end up in that uncomfortable place of trying not to order anything too expensive. Or tip over one of the 8 wine glasses, water glasses, candle arrangements, ehhhh.

Someplace cozy, cheap, not super heavy, with a good beer selection = the ideal!

I have to second what mookie said -- at age 21, most guys will just be thrilled to eat something that didn't come out of a takeout bag or the freezer. If you cook something fresh with TLC, you'll rock his world. Keep the season in mind too.. in the winter, nothing's better than a rustic comfort-food dish like Chicken Marbella (if you google that you'll find the recipe easily) But in summer you don't want to serve something too heavy, especially on a date. I also third or fourth the recommendation to do any prep you can beforehand. It's nice to be able to chat and have a glass of wine before dinner while finishing up the prep, instead of running around like a chicken with its head cut off! Good luck ;)

Oops, it was esmesbell, not PrettyNicola. :P

my homemade chili - so easy, so good.

Pasta tossed with tomato, feta, olives, and whatever leftover meat is lying around the fridge, with fresh garlic and basil

I usually put some brie, currant jam, and slivered almonds into those pre-made phyllo cups. It looks fancy but is a cinch to make... spianch dip in a bread bowl is always a fave too!