Date suggestions. Near matchbox (Milwaukee & Chicago Ave)

First post!!

Well I have a first date with a woman next week and we are going to be meeting at matchbox for drinks and then proceeding to dinner. It is my responsibility to choose where we will be going to dine (a decision which i will undoubtedly be judged on ). If I was with friends, silver palm would suffice, but I dont really want to go there for a first date. Does anyone have suggestions of a nice spot in the general area? Any recommendations would be appreciated.

Thanks!

Coalfire seems like a walkable possibility.

What's your transportation situation? Are you willing to walk? Take the Blue Line? You're not going to find anything else on that corner, unfortunately (unless something has popped up that I haven't noticed).

Are you looking for romantic? Quiet? A scene? Upscale? Casual?

My first thought was Butterfly Sushi (byob) across the freeway on Chicago. West Town Tavern and Flo are over there too.

Leopold or Habana Libre on Chicago Ave

Consider this more dating advice that dining advice... The Matchbox is a 10 minute cab ride from Blackbird, Avec, The Publican, Naha, 160 Blu, etc. Be a sport and take her somewhere nice. Chances are you'll get a second date.

starwarsnut wrote:Well I have a first date with a woman next week and we are going to be meeting at matchbox for drinks and then proceeding to dinner. It is my responsibility to choose where we will be going to dine (a decision which i will undoubtedly be judged on ).

I second the Habana Libre, Leopold, Coal Fire suggestions. If we're talking about being judged, those places just seem like much more interesting, thoughtful choices. Like you actually took time to figure this out. I love Avec, Publican, etc., but I think they're pretty lame, generic, just too easy as date ideas. To throw in another option, I haven't been, but the Black Sheep at Grand and May is walkable from the Matchbox.

Piccolo Sogno.
http://piccolosognorestaurant.com

West Town Tavern is 0.3 miles west on Chicago Ave. Good food, cozy place with nice decor, with looking like you're trying too hard.

West Town Tavern

1329 West Chicago Avenue
Chicago, IL 60622

tel 312-666-6175

http://www.westtowntavern.com/menu.asp

As a local to that area, West Town Tavern would be my top pick as well, with Leopold a close second. Branch 27 is also not a bad choice, but it's substantially louder than West Town.

And Flo would be a great choice for brunch...

I've had two mediocre meals with negligent service @ West Town and two excellent meals w/excellent service @ Leopold.

I've eaten at West Town Tavern more times than I can count over the past 9 years or so (I used to live above there). Although I wouldn't call the service negligent, it's perfectly serviceable to good (in fact, a former WTT server is working at Leopold). I think the food at WTT is more pleasing to a variety of palates. In my handful of visits to Leopold, I've concluded that you eat only from the top of the menu, as the entrees can be abysmal. Both places have a lively atmosphere, and can be a little loud. They're not the candelit, white-tablecloth place that some associate with "romantic" date places (a good thing, IMO). WTT is more consistent; Leopold is edgier.

We actually saw and spoke to you @ the bar going in to what turned out to be an extremely disappointing meal on every level. http://www.lthforum.com/bb/viewtopic.php?t=6269. No one was happy except the house that had our $ in their inefficient hands that night. I returned w/friends one other time since. Underwhelmed was the common denominator, w/o me saying a word and just going along for the ride. For my money, I don't give a place @ this price point more than two tries. For me, finito.

happy_stomach wrote:

starwarsnut wrote:Well I have a first date with a woman next week and we are going to be meeting at matchbox for drinks and then proceeding to dinner. It is my responsibility to choose where we will be going to dine (a decision which i will undoubtedly be judged on ).

I second the Habana Libre, Leopold, Coal Fire suggestions. If we're talking about being judged, those places just seem like much more interesting, thoughtful choices. Like you actually took time to figure this out. I love Avec, Publican, etc., but I think they're pretty lame, generic, just too easy as date ideas. To throw in another option, I haven't been, but the Black Sheep at Grand and May is walkable from the Matchbox.

This is smart advice, assuming she's the kind of girl that might appreciate that you put some thought & effort into planning your date.

I like the Habana Libre suggestion...come prepared with a decent bottle of wine, or even a tightly-sealed container of mojitos that you made earlier (and a couple sprigs of fresh mint), bring the beverages out at dinner, and have a nice, soulful meal in a casual, energetic environment. Come to think of it, I should steal this idea for date night with the wife (she's a huge fan of taking containers of pre-made cocktails to BYOB places, so she would definitely approve of the mojito idea).

Avec, Publican, Blackbird, and their ilk for a first date might make you look like the kind of guy who tries to impress by throwing money at things rather than through thoughtfulness & creativity. Now, if she's the kind of girl that might appreciate that, then, to quote Kanye, "now I ain't sayin' she a gold digger...."

Without question...patio at Picolo Sogno.....make reservations early....you WILL impresss..

Coalfire..while great pizza, is not a date place (especially first date)...

Jazzfood wrote:We actually saw and spoke to you @ the bar going in to what turned out to be an extremely disappointing meal on every level. http://www.lthforum.com/bb/viewtopic.php?t=6269. No one was happy except the house that had our $ in their inefficient hands that night.

Yeah, I was there, had a different experience. Typically, whether someone enjoys their meals out depends upon their expectations and their attitude going in. Maybe your underwhelming first experience colored your second? Who knows. Just datapoints.

Khaopaat wrote:Avec, Publican, Blackbird, and their ilk for a first date might make you look like the kind of guy who tries to impress by throwing money at things rather than through thoughtfulness & creativity. Now, if she's the kind of girl that might appreciate that, then, to quote Kanye, "now I ain't sayin' she a gold digger...."

I'm more of a Jay-Z gal myself. "Money ain't a thang..." (Turn it up.)

ParkLaBrea wrote:Without question...patio at Picolo Sogno.....make reservations early....you WILL impresss..

Unless it's 100 degrees outside - then stay indoors for the A/C.

But yes, the patio works wonders.

Indeed......unless too hot....still nice inside though...

Plus, it is only one very short stop away from Matchbox....practically right next to the Grand exit.....so you/she won't get all mussed up in your first date duds walking there...

Ahhhhh..first dates.....I remember those....

ok.... First of all, you wrote ....

If I was with friends, silver palm would suffice, but I dont really want to go there for a first date.

ummmmmmmm don't you want to be her friend also?

Did you ever think of asking her - where she might like to go??? She might even suggest Silver Palm? The food is good. So what if its an old Railroad Dining Car? There are many women that still relate to a NOVEL idea for their first date.. not just the food or how much you spend.

Ok.... Not silver palm... How about across the street -- D'Agostino's ------ Good food reasonable prices. Unfortunately it can get a bit loud and roudy.

Another suggestion.... on Grand ave just east of Ogden -- SALERNOS. Often forgotten because it's NOT a HIP DATE PLACE ..and is considered more of a place where married or old retired folks go. But Salernos has been around for years and offers good food at resonable prices... and a more romantic atmosphere.

While we can recommend places -- GO SOMEWHERE you are familiar with and that you like.

Hopefully she will like it also. Because, if she does like it and you hit it off... that means you will probably go there many times to re-live the memories of that first date.

If you go somewhere recommended by us... and you don't like the food or atmosphere... and SHE DOES... remember --- you'll have to go back and smile thru lousy food while pretending you like it ... all the time wishing ... why didn't I go to the Silver Palm?

West Town is my choice, too, when I'm in the area for slightly upscale (i.e, beyond diner/ethnic-storefront/pizzeria) dining and I have never been disappointed in the ambience, the quality of the food, or the service. As far as ambience is concerned it's several steps above D'Agostino's, Havana Libre, and Coalfire all of which I like but all of which I consider pretty casual (altho if that's what you're looking for Coalfire-- a bit further away, of course -- would be my choice). West Town also has the advantage of a fairly eclectic menu, appealing to a variety of tastes (it even has an excellent steak option). In the same range, Piccolo Sogno is an excellent choice, too, altho it was recently featured (very positively) on Check Please, and might still be dealing with some overflow.

Further down Chicago on Ashland is Ruxbin. They don't take reservations, but I thought I'd add it to the mix, since it looks like a fun place for a date.
http://www.ruxbinchicago.com/site/?page_id=8

A little advice from IDID...do not take her to D'Agostinos if you want a 2nd date. IDID learned that the hard way.

Another thought, if you are willing to walk a bit farther west, is Mexique.

If you were to use GDine to prepay for the prix fixe meal, which is mighty good, and offers reasonable choices, you'd have a fine meal, in a chic place.

And you could always cross the street, head a bit farther west, for dessert at Hoosier Mama Pie Company!

I don't care what she says, I'm taking her to Coalfire if I'm near that intersection. But seriously, it's a great place for a date. Awesome pizza, nice atmosphere, great service, what more do you need?

Then I would get some custard at Scooters, though it might be a little crowded these summer nights.

Dare I throw Cafe Central into the mix?

rfleisch1 wrote:And you could always cross the street, head a bit farther west, for dessert at Hoosier Mama Pie Company!

Just remember that Hoosier Mama is only open until 7pm during the week, 9pm on Fridays and 5pm/4pm on weekends.

Ram4 wrote:Then I would get some custard at Scooters, though it might be a little crowded these summer nights.

I love Scooters, but Black Dog Gelato is a little closer. I stole this from Hellodali, but the best date ever in this area is early cocktails at Bar DeVille, BYO dinner at Habana Libre and Black Dog Gelato to cap the evening.

One of the worst first dates I ever went on started at Matchbox. Word to the wise: don't slam tequila shots in front of your date, even if it comes with your beer as a special.

West Town Tavern would probably be my choice for a date - nice, low key, decent food, and not a scene so you can hear your date talking.

Have fun!

essie wrote:One of the worst first dates I ever went on started at Matchbox. Word to the wise: don't slam tequila shots in front of your date, even if it comes with your beer as a special.

West Town Tavern would probably be my choice for a date - nice, low key, decent food, and not a scene so you can hear your date talking.

Have fun!

hmmm...anyone I know? This is intriguing miss Essie

happy_stomach wrote:

rfleisch1 wrote:And you could always cross the street, head a bit farther west, for dessert at Hoosier Mama Pie Company!

Just remember that Hoosier Mama is only open until 7pm during the week, 9pm on Fridays and 5pm/4pm on weekends.

Not to mention they'll probably run out of what you want long before they close.