mbtmsu

her-27 year old stylist, not into the bar scene anymore, but loves to go to new cool food places, lives at jefferson park blue line stop

me-23 year old consultant, lives in gold coast, semi-foodie, but very picky eater (no seafood, sushi, indian, or anything new-age and crazy), prefer italian, mexican, steak

when-monday night

where-??prefer something in the gold coast/LP/river north areas

i would prefer something that isnt too extravangant, so as not to intimdate the lass (so no trotters, tru, ambria, etc.). but at the same time, she is an "older woman", and i feel like i need to impress.
please send your suggestions (frontera grill?) for a first dinner date, and bottle of wine for under $75

Sweet Willie

Chef Shawn McClain's Custom House Restaurant perhaps ?http://www.customhouse.cc/dinner_frame1.html

Printer's Row area.

--

DataPlumber

Adobo Grill - Mexican
Twist - Tapas

Gargoyle

Just don't go to Leonas. In my young single days, I went on three first dates at various Leonas. They were also last dates, which became clear before the main course was finished. The place is a jinx.

chgoeditor

Two suggestions:

Coobah--Nueva Latina on Southport just south of Addison, good vibe, great summery place (after all, it's a cuisine of warm climates), a lot of interesting mixed drinks, plus a wine list. You'll see a lot of 20 and 30somethings on dates here...it usually attracts a good looking crowd (but don't get me wrong...the food is great). One interesting piece of trivia...the owner/chef is the former drummer for the band Veruca Salt

Terragusta--a newish Italian restaurant that's getting a ton of buzz for its homemade pastas and use of fresh, local, organic ingredients. Most dinners recommend sticking to appetizers, salads and pastas, and skipping the entrees (meats). It's BYOB...stop in Binney's for a great Italian recommendation. (located on Addison & Wolcott)

Socca--I think the owners describe it as a French/Italian country-style restaurant. Good mix of meat, poultry, seafood and vegetarian choices. If you want to assemble a grazing menu of appetizers, salads and pizzas, you can do that, too. A relaxed/upscale atmosphere (but definitely adult)...you're not going to see a table full of loud 21 year olds here. At the corner of Clark & School.

You'll find all on Metromix.

(BTW, I have a fourth date on Monday, and I'm considering both Coobah and Terragusta. We went to Socca for our first date.)

One note: If the Cubs are in town on Monday, you'll want to take a cab or consider valet for Socca/Coobah...it might not be an option at Terragusta.

mbtmsu

any other suggestions for activities on this date? low-key bars to hit up after dinner? musuem trip? show?

DataPlumber

Coobah has GREAT drinks. The food can be hit or miss. The appetizers and tamales are awesome. Maybe it's us but we've been served poorly prepaired fish entress on several occasions. Everytime they were horribly overcooked and dried out.

chgoeditor

I must admit that I love their Chicken Negra Modelo, and order it almost every time I'm there (which is only once or twice a year). I'm much more of a fish eater, so it's odd that I'm hooked on a chicken dish, but I get a craving for this one from time to time. Thanks for the fish tip, though.

chgoeditor

If this is a first date, I'd stick to dinner and *maybe* suggest a quiet bar afterward, but nothing else. The key to a great first date is leave you both wanting more. (This assumes you don't know each other too well, i.e., you aren't platonic friends who are seeing if you have the potential to be something more serious.) In my opinion, it's better to err on the side of a first date that's too short, rather than one that's too long and has her looking at her watch thinking, "When is this going to be over?" (Even if you have nothing to do with the reason she's only thinking that--maybe she has a busy day at work on Tuesday, or she's worn out from the weekend--it will still leave her with a bad impression.)

Don't go to a show or movie on the first 5 or 10 dates...you can't talk to one another, and the entire point of dating is getting to know one another.

A museum date is a good Saturday or Sunday afternoon date, maybe combined with lunch somewhere downtown. Leave that for date number three or four, when you're confident that you want to spend 5 or 6 hours with her.

(In case I need to establish my "date cred," I'm a single, city-dwelling woman in my mid-30s. I've been in long-term relationships, but my most recent one ended last summer, so I've done my share of dates.)

mbtmsu

great advice, thanks...unfortunately, i don't have alot of experience, as i have spent the last 20 some years with my nose stuck in a book or my ... working

and i've only been in chicago for about a year, with m-f on the road for work

GeoGirl

I like Rosebud on Rush . Pros: The food is great and it's a classic and not too expensive. Cons: It's a little noisy and it may not be quite as hip as other places.

I'm not a Chicago native or resident, just go there a few times a year. And we almost always go to Rosebud. Maybe it's a touristy thing, I don't know. LOL Just thought I'd throw in my rec.

GG

chgoeditor

The food at Rosebud is great! I don't go there a lot, but it's delicious. The downside: If she likes cool new places, she might not respond well too it.

Since the OP's date lives in Jefferson Park (which is NW side, right?) and the OP lives in the Gold Coast, I'm trying to think of places that are more in the middle so neither of them has an outrageous cab fare to pay. (For example, I think Butter or David Burke's would be great recommendations, but the OP's date would pay $30-40 in RT cab fare, which is pricey.)

Just checked and the Cubs are playing at home and a night game on Monday...some Lakeview, Uptown and North Center will all be traffic headaches, though they'll be able to get there by cab and should be able to get a table.

chichow

opinions on Terragusta...the reviews are scattered on Metromix

chgoeditor

Chichow, a lot of people believe that Metromix doesn't print every review it receives (particularly bad ones), and, therefore, it's reviews are suspect. LTHForum.com, which is primarily Chicago-restaurant oriented, is a much more dependable source of restaurant info from dedicated eaters in the Chicago area.

Here's a thread from there on Terragusto:
http://www.lthforum.com/bb/viewtopic...ght=terragusto

I ate there with a friend on a Friday night about a month ago. We had a reservation and were seated promptly. Because I'd read reviews suggesting we skip the meat dishes, we ordered and split two appetizers and two pasta dishes. We also received fresh bread and butter. This was a great move, and left us feeling comfortably full, but not stuffed. We passed on dessert and coffee.

Our appetizers were a fresh asparagus salad and mushrooms over polenta. Both were great! As you've surely read, Terragusto's emphasis is on fresh, organic and locally sourced ingredients. (In fact, if you drive by the restaurant during the day, you're likely to see them rolling pastas in the front window.) In the asparagus salad, in particular, you could just taste that the flavors were bright and the salad was well-constructed.

Unfortunately, I don't recall the specific details of our pasta entrees. I know we got a spaghetti or spaghettini, and a ravioli, but I can't recall the toppings on either. In any event, we finished both.

I'd definitely go back to Terragusto, and I'd recommend it to other people who appreciate restaurants that are putting extra care into the food, and people who are willing to pay for that effort. If your standard for good Italian food is, "How big is the platter of pasta?" then Terragusto is not your restauant. (In fact, I was thrilled because the pasta portions were actually reasonable portions.)

I hope this helps!

ElmhurstNick

It's been a while since I've read LTH. They do know their food, but one caveat is that they are not particularly concerned with decor. Not usually a big deal, but for a first date, some LTH favorites such as Ed's Potsticker House might not be the best place from an ambiance perspective.