Not from the area but have a colleague who will be traveling to The Woodlands (Staying at Hyatt Centric). Asking for restaurant recommendations... Probably looking for reasonably-priced cool places.

I'm just get this outta the way once and for all...

Chilis
Applebees
Cheesecake Factory
Joe's Crab Shack
Outback
Cheddars
On the Border

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Not from the area but have a colleague who will be traveling to The Woodlands (Staying at Hyatt Centric). Asking for restaurant recommendations... Probably looking for reasonably-priced cool places.

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Step 1: Get on the hardy toll road and drive the 25mins South to Houston

Step 2: Pick a place...

All the food around Market Street is suburban bullsh t. Pretty generic and forgettable. Does that matter to your colleague? If not, he/she should be fine anywhere.

If it does, get out of The Woodlands as suggested.

When you say "reasonably-priced, cool..." what kind of age range are we looking at?

That really plays a part in this decision...if he/she is under the age of 35, then there is really no reason to eat in the woodlands and expect decent ambiance or crowds. It's just a bunch of divorcees and 40 plus year old men who still wear glitter on their shirts like it's 2006...or worse, it's a bunch of rude ass transplants.

But when I do eat out there...
Local Pour
Escalantes
Fogo de Chao
Uni Sushi
Cureight
Cyclones
Crisp

All of the suggestions above from schmendeler and fatrandy are good. I'd also add Kona Grill and Cru wine bar to the list.

If your friend wants to go downtown, that's fine, but it's not even close to a 25 min trip on a weeknight (assuming he/she wants to eat before 9 pm). More like an hour to an hour and a half trip.

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If your friend wants to go downtown, that's fine, but it's not even close to a 25 min trip on a weeknight (assuming he/she wants to eat before 9 pm). More like an hour to an hour and a half trip.

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Closer to 30 mins

Schemendeler has the best list of places unique to The Woodlands and a different atmosphere from a chain.

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All of the suggestions above from schmendeler and fatrandy are good. I'd also add Kona Grill and Cru wine bar to the list.

If your friend wants to go downtown, that's fine, but it's not even close to a 25 min trip on a weeknight (assuming he/she wants to eat before 9 pm). More like an hour to an hour and a half trip.

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If it's taking you an hour or an hour and a half, you are not driving fast enough or aren't taking the Hardy. I live right off Sawdust and going South on the Hardy after 5pm is virtually wide open. At most, it's taking 40mins with a traffic. Either way, I'd rather drive 40mins to eat and drink in Houston, than do any of that in the Woodlands.
Although the Hardy has been usually closed on the weekends lately.

Also, I would've put Kona on my list as well, but last time we ate there, 5 of us got food poisoning.

Had a good experience at Amerigo's.

I've had it take as long as 30-40 minutes just to get from Woodlands Pkwy (which is roughly where she'd be coming from) to the Hardy, when traffic is backed up. The Woodlands Pkwy/45 interchange is absolute gridlock (that really extends from Lake Woodlands to Rayford/Sawdust, including I-45 and the frontage roads) from about 5 pm to 6 pm.

Last time I drove downtown on a weeknight, I took GP to 45 (I live south of the Hardy, so it's not always convenient to get to it), and it took an hour and a half because there were two wrecks.

If she checks traffic beforehand, and it's clear, she could get downtown in under an hour. But that's a big if, considering there are probably at least 1-2 wrecks a week.

In Market Street, Jasper's easily is the best restaurant. It's a Kent Rathbun creation. Serviceable alternatives are Grotto, Uni Sushi and Tommy Bahama Grille.

In Waterway (the riverwalk area), Hubble and Hudson is excellent but pricey. Americas is very unique if you're into that sort of thing and also pricey. Cyclone Anaya's is pretty solid Tex-Mex. Also, if it's a wine bar that you want Crush is a better option than Cru, which has very limited food. All four of these are in the same block.

At the mall, Flemmings is a good traditional steak house, or Kirby's which is on the southbound I45 feeder at Woodlands Parkway. Haven't been to Kirby's since they were putting in a cigar lounge. If they require the regular smokers also to use the lounge, then Kirby's bar is a great place for table of 1. Lastly, Guadalajara Hacienda is worth checking out for more traditional Mexican food and arguably the best chips and salsa.

All of the spots on restaurant row at Hughes Landing are crowd pleasers. Favorites are Truluck's (real seafood), Blue Fin (sushi, better than Uni), and Local Pour (huge bar, beers on tap but also good food).

Just about a mile over on Research Forest, there are also some good choices. Bob's Chop and Steak House is the best in town IMO short of Pappas Bros and perhaps Vic & Anthony's. As mentioned, Fielding's Wood Grille is also popular (farm to table). And Ruggles Green and Black Walnut are both worthy of a visit for more casual fare.

Going a little deeper into Woodlands Parkway, The Republic Grille is much like Fieldings and Ruggles. All the way back to Kuykendahl you'll run into another steak house, Perry's, and the best Italian in North Houston, Via Emilia.

There is plenty of very good dining in The Woodlands.

I also really like Guadalajara, and have heard great things about Bob's (although, I haven't been there myself).

Anything that's not at Market Street or on The Waterway is going to be typical suburban clientele...SAHM moms happy to have a night out, dads tired from a long day at work, and screaming kids. Market Street, The Waterway, and Hughes Landing can attract a decent young-ish happy hour crowd, since there are some big companies with offices up here (although, last time I went to Kona, there were screaming kids there, too).

I have not experienced it myself, but apparently the bar scene gets a little...um, shall we say "alternative"...on certain nights at Tommy Bahama and Jaspers. I know a couple of people who have been propositioned to participate in some group activities while hanging out at the bar there.

Yeah, that traffic can get pretty bad around the Mall and market Street area, there are usually a few backs ways to take..but she obviously wouldn't know that. After 6 it clears out a bit though, in that area. It only takes me about 5 mins just to get on the HTR, but if you're south of it, then yeah you are definitely SOL after 5, now I see why it takes you so long.

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I'm just get this outta the way once and for all...

Chilis
Applebees
Cheesecake Factory
Joe's Crab Shack
Outback
Cheddars
On the Border

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The closest Cheddars is near Splashtown and
I can't recall there being an applebees there.

There are a lot of chains but I have been happy to see some new unique places show up there recently.

To the OP, Some other more relaxed atmospheres:
Grub
Ruggles
Crust
Yucatan

Robard's or Hubbel and Hudson.

Had a great meal at Fielding's last Saturday night.

Italian: Amerigo's, Via Emilia
Mexican: Los Cucos, Guadalajara, Escalante's
Steaks: Robard's, Fielding's, Perry's
Seafood: Truluck's

Hubbell and Hudson

The Refuge
Grimaldi's Pizzeria
Schilleci's New Orleans Kitchen
CR Food & Wine Bar
Via Emilia
Trulucks

Red Brick Tavern in Conroe.

Thanks everyone for the replies... Definitely helpful! I'll check back in and let you know how it went. FWIW - colleague is late 40's and meeting a business associate who is flying in from Chile.

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Mel's in Tomball.

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I once was eating at Mel's when a table next to me waved down a waitress on her way back to the kitchen. There seemed to be a booger on their table and they pointed it out to the lady. She looked down at it, looked up at them, back down, and with an index finger wiped up the booger and onto the towel on her belt. She then proceeded into the kitchen and then back out with a tray of food. We were all truly stunned.

To this day Mel's gets the booger veto when suggested to me.

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booger veto

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Using this forever.

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I also really like Guadalajara, and have heard great things about Bob's (although, I haven't been there myself).

Anything that's not at Market Street or on The Waterway is going to be typical suburban clientele...SAHM moms happy to have a night out, dads tired from a long day at work, and screaming kids. Market Street, The Waterway, and Hughes Landing can attract a decent young-ish happy hour crowd, since there are some big companies with offices up here (although, last time I went to Kona, there were screaming kids there, too).

I have not experienced it myself, but apparently the bar scene gets a little...um, shall we say "alternative"...on certain nights at Tommy Bahama and Jaspers. I know a couple of people who have been propositioned to participate in some group activities while hanging out at the bar there.

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Do Tommy Bahama or Jaspers have two chairs out front in the grass? That's your signal that some kinky stuff is about to go down.

Does you like Family Guy?

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Mel's in Tomball.

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I once was eating at Mel's when a table next to me waved down a waitress on her way back to the kitchen. There seemed to be a booger on their table and they pointed it out to the lady. She looked down at it, looked up at them, back down, and with an index finger wiped up the booger and onto the towel on her belt. She then proceeded into the kitchen and then back out with a tray of food. We were all truly stunned.

To this day Mel's gets the booger veto when suggested to me.

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That's how you know it's good. That and a little ash seasoning from the chef

Is wearing a Tommy Bahama shirt while dining at Tommy Bahama encouraged or frowned upon?

encouraged but only if done unintentionally. like, you were wearing it just because it was in the rotation.

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Mel's in Tomball.

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I once was eating at Mel's when a table next to me waved down a waitress on her way back to the kitchen. There seemed to be a booger on their table and they pointed it out to the lady. She looked down at it, looked up at them, back down, and with an index finger wiped up the booger and onto the towel on her belt. She then proceeded into the kitchen and then back out with a tray of food. We were all truly stunned.

To this day Mel's gets the booger veto when suggested to me.

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That's how you know it's good. That and a little ash seasoning from the chef

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I ordered the chicken fried steak!

At least she didn't say, "You think it's a booger but it's not."

At Mel's stuff like that happens right out in the open. At all the expensive places it's happening where you don't see it.

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I also really like Guadalajara, and have heard great things about Bob's (although, I haven't been there myself).

Anything that's not at Market Street or on The Waterway is going to be typical suburban clientele...SAHM moms happy to have a night out, dads tired from a long day at work, and screaming kids. Market Street, The Waterway, and Hughes Landing can attract a decent young-ish happy hour crowd, since there are some big companies with offices up here (although, last time I went to Kona, there were screaming kids there, too).

I have not experienced it myself, but apparently the bar scene gets a little...um, shall we say "alternative"...on certain nights at Tommy Bahama and Jaspers. I know a couple of people who have been propositioned to participate in some group activities while hanging out at the bar there.

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Do Tommy Bahama or Jaspers have two chairs out front in the grass? That's your signal that some kinky stuff is about to go down.

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Haha! I was waiting for someone to bring that up! Both have outdoor patios, so IDK if that counts as chairs out front. But, based on the reactions I get from people when I tell that story, I don't think they need them. I doesn't seem to be a secret.

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encouraged but only if done unintentionally. like, you were wearing it just because it was in the rotation.

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+1