What food will win him over?

That answer has been different for every man who has ever been in my life. There's no way to answer the question adequately without asking him his likes and dislikes.

In the end, always go with dishes you are comfortable preparing, but there should be some overlap between what you like to cook and what he likes to eat, no?

I would give the same advice I [try to] tell myself when entertaining: make something you are comfortable and confidant in cooking, as in something you've made before and loved eating. And then pair it with sesame noodles. OK I am only half kidding about the sesame noodles - I tend to make them for picnics and potlucks, and guys seem to like them?

my go-to dish for first timers eating my food has long been pork chops with pan gravy; as long as they eat meat, it's totally easy, totally quick, and totally delicious. my girlfriend was never a huge porkchop girl until she had mine, and now we'll be married this fall! (probably has less to do with the chops, but they certainly didn't hurt).

In any case: smear your chops with spicy brown mustard, let them sit for a few hours in the fridge, then fry them in a cast-iron skillet. Set the pork chops aside, pour in some heavy cream, salt and pepper to taste (consider some more mustard), scrape all the goodness off the bottom of the pan, and add a thickener (i like to use corn starch).

Serve it with some kind of green veg and mashed potatoes (i like to use sweet potatoes, seasoned with nutmeg and pepper) - they're great with the leftover gravy :-)

Also, for a romantic take on why the pork chop is such great date food, I highly recommend Homesick Texan's recent post about them: http://homesicktexan.blogspot.com/2011/06/pork-chops-jalapeno-beer-brined.html (also sounds like something worth trying).

I agree--it's about sharing who you are as well as finding out what he likes. When my husband and I were dating, I went through a fancy shepherd's pie kick. I made him a new elaborate shepherd's pie in an individual ramekin every week. (He swoons over mashed potatoes of any sort.) Even now, every time I make one of those he's giddy.

Good combinations:
- beet and sausage filling with gorgonzola mashed potatoes
- beef meatball and marinara filling with mashed purple potatoes and parmesan ("Tuscan Sunset")
- white bean, spinach, kale filling with gruyere and caramelize onion mashed potatoes

Love drbabs take on things. It is about you sharing yourself with this guy. And finding out what his tastes are. And here is a tried and true recipe that ignites - always a hit when I make it. From ChefJune http://www.food52.com/recipes/10695_flambed_chicken_with_tomatoes_and_garlic

Maybe take a look at Pizza Maker's Steak. Very easy, inexpensive, and (no pun intended) flashy.

http://www.food52.com/recipes/10718_pizza_makers_steak

First, find out what he likes. Second, make sure it's something simple, but impressive. Third, it has to be something you like, too! When my husband & I started dating I already knew he has a chilihead, too. I invited him over for dinner on his birthday (first time cooking for him). I made him Bajan Chicken one of Dave DeWitt's recipes. Lots of habaneros and allspice. It was love at first bite...
Good luck & have fun!

What food says "you?" What do you make that represents who you are, what you love, and how you share your love through cooking? If he's the right guy, that will win him over. (And if he's not, you might as well find out now...)

I don't know about your boyfriend, but husband is a dessert man. You can't go wrong with KelseyTheNaptimeChef's chocolate bundt cake: easy recipe, simple instructions, and a truly incredible cake! I don't have a bundt pan, so I used a round spring-form cake pan and have enough batter to make a small loaf of cake. http://www.food52.com/recipes/2835_chocolate_bundt_cake

I used to make Steak Diane for the beef lovers. It isn't very difficult, just don't overcook the meat. I use the recipe from Piret's Bistro cookbook but I can't find it online to point you to it.

If you have a fish lover, you can't go wrong with the Halibut from Alfred Portale 12 Seasons, note to self to get this book, it's on epi. Not difficult, green beans are in season, and it is restaurant quality dish to serve. Delicious.
http://www.epicurious.com/recipes/food/views/Seared-Halibut-with-Haricots-Verts-Scallions-and-White-Wine-Sauce-104104

For this season I might make some marinated chicken and veggies (some combination of onion wedges, zucchini, eggplant, asparagus, tomato) on the grill. Maybe a corn and bean and tomato salad. Everyone likes that, as long as you don't overcook the chicken and make it dry. Serve a decadent dessert with it. I usually marinate everything in yogurt with lemon juice and zerst, sautted onion and garlic and some curry powder. Skewer each item separately so each is done just right, but put onion with the meat, caked all over with yogurt and grill.

I don't think there is any food that is "universally loved."

You need to ask him what he likes.

My husband is the easiest person in the world to cook for. If I would make meatloaf every week, he'd be happy. He also really likes spaghetti. Both those things are easy to make.

Pasta w/ vodka sauce is always a good bet: http://www.food52.com/recipes/9134_penne_with_tomato_vodka_cream_sauce
A simple salad and some crusty bread would round out the meal.
And for dessert, chocolate mousse: http://www.food52.com/recipes/2908_chocolate_mousse_with_cointreau_and_chocolate_shards