Riddle’s Penultimate Cafe & Wine Bar

Always our fav place to go in the Loop. Loved to hear Swirl there. The perfect evening. Sometimes dropped 100 $+ and didn’t care cause it was great. Then something bad happened. Now the food sux. The service staff just doesn’t care… breaks my heart that I can’t go to my fav place anymore. Need Andy to take it over again or need it to close forever so that it is at least a good memory. Sorry.
This place has closed.

Chilled orange apricot soup (excellent), tortellini soup (pretty good), Chicken Major Grey (very good and came with squash as my side — excellent) and stuffed mushrooms (burnt?, not so good) and a pasta dish I can’t remember right now. Only getting 3 stars because was a bit pricey for the food, service while good lost track of part of our order. Not sure I would go back when there are so many other places. Maybe to check out the live music.

I do not usually give 1-​Star reviews, but I felt inclined when I recalled my two experiences at this establishment. The service was just tragic. It took forever for each course, and it seemed that they only had a few employees on staff as well. I’m not a huge wine buff and cannot speak to their wine list and quality. However, the food was less than phenomenal and highly overpriced. The interior also looked like it hasn’t seen a dusting since 1945. It was a disappointing and expensive adventure.

Over the years, my bf has eaten at Riddles quite a few times. Last night, we went there and were both astonished at the poor quality of service and food. We arrived at 7 and did not have our appetizers until 8:15. We had to ask for bread rolls, and the rolls were hard as a rock. The mushroom appetizers arrived cold and had tooooo much butter. The entrees arrived at 9:15, and my bf commented that the ingredients didn’t seem fresh as they used to. By 9:30, we were sucking gas fumes from the idling SUV parked within a foot of our table. We were weary of the large groups of wandering suspicious looking teens. And we still had not finished our meal. The inside of the restaurant was sooo smokey and loud that it was not an option. Recently, they have raised their prices. So appetizers average about $ 10 and entrees average about $ 20 — $ 25. I understand that Friday nights are restaurants’ busy nights, but this was ridiculous. The only attentive person was the bus boy. We never got an apology about the slowness of the service. If you want overpriced, butter drenched food with cold and tired produce and ridiculously slow service in a smokey (or dangerous) environment, then this is the place for you. Enjoy! We will be staying away for a long time.

I only came here once to watch the Jazz trio. They were pretty amazing to listen to and everyone was having a good time. People who were there for some drinks would just talk over the music; others were there to enjoy the music (like we were) and some even got up to dance a bit (there’s no danceflloor, so just spontaneous dancing, haha).
Décor: Bar on the left, restaurant on the right and deep inside was a curtained off area where I think someone had some private party, so I don’t know what the inside was like.
They had an EXTENSIVE wine list, which can get sort of pricey if you’re there for a while. We had some strawberry shortcake, which was, meh, okay.
Bottom Line: If you’re into this sort of loud/​music/​chillax scene, this would be it!

Love this place! Conveniently located on the Loop, Riddles has a great selection of beers, including the delicious HopSlam, and the live bands are always great. It’s a small bar so it can get a little noisy at times, but there is outdoor seating where you can still enjoy the music. Never eaten food here but my friends say dinner is da bomb.

This place really suprised me. We decided on a whim to check them out one night. A few people had told me that they had great food but when we walked in the door I thought they were yanking my chain.
When you walk in it’s a full on bar atmosphere but when you let them know that you want to eat they take you to the back room. Don’t let the décor fool you either (very 1960’s banquet hallesque) cause this place has great food!
Local, seasonal ingredients and very fresh. We had the duck and the steak and both were excellent. Really good flavor and cooked perfectly.
And, for anyone else who searchs for this, they are really knowledgeable about gluten free and modified one of the sauces in order to make it safe for us.
Will definitely be back!

Amazing food and wine/​beer list.
Very smokey and loud… but the bands are usually good!
Definitely would recommend to jazz fans on Wednesday nights.

Nice place and a TOTAL surprise!
We were recommended to eat here from Global Gourmet (Tippy) so we thought we would give it a try. As you enter the place, it looks like a bar, but once you tell them you want to eat there, they lead you to the back of the house where the atmosphere is completely different. This was the biggest surprise.
The beer was good, you can’t really go wrong with beer. The food was good.
I had an English dish with beef and bread. I can’t remember what it was called… but the waitress recommended it and I’ve never had it before, but we ate all of it. I say we, because my fiancé helped me finish it.
My fiancé got the Duck L’Orange Pasta — it was good, but a little rich for our taste.
Our friend got the Pasta Tutta Mare — his was de-​lish.
Overall, we like the place and would probably come back and try other things on the menu.

They smoke their own salmon; they sauté locally-​grown shiitake mushrooms. The emphasis is on local ingredients.
Attentive service.
All in a room that looks unchanged since the 1960’s

I hadn’t been to Riddles in years. I’m so glad I re-​discovered this classic gem of the Loop’s (now decades old) renaissance.
Riddles is really two different establishments. At one you have the locally sourced menu of Cajun/​Creole inspired food and features one of the best wine lists in the area. Everything I have ever had is darn good. At the other, you have the smoky dive bar, that features live music what seems like every night, and whose interior doesn’t look like its changed much in 20+ years its been open.
I think the real riddle of Riddles is how this dichotomy works so seamlessly. Last night I had a great meal with my family, fun but tame parents included. Once they went home, friends joined my siblings and I for a night of drinking and conviviality. There was a great two-​piece country band cranking out standards, as well as, originals. We closed the place down and were all the better for it. The server was friendly and the environs were just right for sometimes silly and sometimes poignant conversation.
If you’ve never been, give Riddles a shot. If you’ve waited to go back, there is no time like the present.

Really good food here, I loved the fresh and local menu. The atmosphere is a strange but likeable mix, live music (classic country the night I went), hipster staff… sitting outside on a summer evening is a good spot for people watching. I also thought the beer list was pretty impressive as well as the wine options.
I had the Chicken Rose which, according to the menu, was a «staple» of the restaurant. It was damn good. I enjoyed the no frills nature of this place and the eclectic menu and crowd that was milling about. Price was reasonable, too. 2 drinks, meal and dessert for under $ 40, not too shabby.

Love it. Went here with a group of four, and everyone loved what they got — chicken paprikash, spinach lasagna, cavatelli and broccoli, pulled pork, stuffed mushrooms, side dishes… not a bad item was ordered. Most entrees are in the $ 20 range, and that usually gets you a salad or soup and/​or a side dish. The menu isn’t huge, but it’s varied enough that most people should find something they like.
The wine list, as you might imagine, is really extensive, and the beer list is fairly large as well.
The place was somewhat busy but not overly crowded when we went on a Friday evening around 8:30. The service was slow, but this isn’t the kind of place most people go to rush.
All in all, a good experience.

My recent meal at Riddle’s was horrifying. I was absolutely mortified as I had selected this place and we had 9 people join us. We arrived at 6:30; we ordered our food at 7:15ish; entrees arrived at NINE. When they arrived, exactly one was hot. Two were stone cold, and the rest lukewarm at best. A friend’s chicken paprikash actually had sauce that had formed a skin, and was so dry inside that when she cut into it it looked like dried coconut. My halibut was both cold and dry and lacked any flavor whatsoever. The asparagus was overcooked. The spinach was undercooked. Several of my friends said their meals were tasty, except for the not being warm part, but who can enjoy food that isn’t served at the proper temperature?
They were out of the red wine we ordered. They were out of the most interesting soup at 7 PM. The white wine we ordered had completely gone off. They said it would be 7 – 8 minutes to chill the next bottle we ordered. It was forty. In fact, when he brought our entrees and we asked after the white wine for the second time, he explained quite snottily that he hadn’t been able to get it yet as he’d been getting our food ready to carry out. (Isn’t that what a kitchen staff is for?) He would also disappear for huge amounts of time; my husband waited a half hour for a refill of a Diet Pepsi.
At the end the server was apologetic and tried to comp us dessert, but at that point it didn’t matter. The evening was completely ruined. Also, we didn’t have another hour and a half to wait around while dessert was served to us. Nothing could induce me to set foot in that place again, especially after we exited the restaurant and saw servers swarming around the sidewalk tables. Everyone seemed to be having a good time. We’d been out to have a good time and instead had a terrible, terrible evening.
If you can’t handle a big party, don’t take a reservation for one. I had a sinking feeling when I saw that our table was all the way at the back of the restaurant, separated from everyone else by a wall. That can often end badly.
And why does a restaurant that serves entrees that can cost upwards of $ 20 or more have servers that look like they just rolled out of bed and are still hungover from the previous night’s partying? Ties aren’t necessary, but perhaps you might get your waitstaff to dress like they didn’t skateboard to work.
Why serve local food if you’re going to cook it horribly? The crimes they committed against that organic chicken, pork and fish won’t soon be forgotten. Fortunately my friends have good senses of humor.
It was honestly the worst meal I have had in St. Louis yet, and one of the worst I’ve had ever. I’d have given it zero stars, but that doesn’t seem to be a Unilocal option.

Love-​Live jazz, extensive wine list, modest but yummy draft beer selection. Great big wooden booths to sit in. It’s definitely a place you can go after a long day and relax. No pressure. AWESOME staff. They are ALWAYS nice. I’ve never had bad service there. I also love that they have a non-​smoking outdoor seating area. It’s between buildings, but fear not claustrophobics, there are beams with ceiling fans, so the air is fresh. It’s bricky and candlelit and romantic.
Not love-​The food is terribly hit or miss. I had the worst pesto pasta of my life there. But I also had an orgasm-​inducing goat cheese bruschetta. The entrée spinach lasagna is like 15 dollars… It’s yummy, but a little steep if you ask me. By the look of the place, you’d think the food prices might be a little more affordable. From what I understand, they try to buy local. I had the fresh tomato salad and, girrrrl, they were straight out of the garden.

Riddles is the bomb. I have been going there for 5 years and it never changes. They have a wonderful selection of beer and wine. Although the food is pricey, it is absolutely delectable. This is gourmet dining at its best. From the light menu cheeseburgers to the hand picked fresh fish and local veggies its all delicious. If you go in the summer, make sure you try the gazpacho. Mmm…
But those aren’t the reasons to go to Riddles, no no. People go to Riddles because of the atmosphere and surroundings. You will find people of ALL ages here, from ¹⁸⁄₂₁ to 50+. There are no dirty looks from anyone and when the band is going (folk/​jazz/​blues every night of the week) you will often find a few dancing in the aisles. The outdoor seating in the summer is wonderful and even though its often busy, you can nearly always get a table immediately. The service is very good too.
The ONLY bad thing: if you are hard of hearing and want to have good conversation, you will need to sit in the back non-​smoking room or outside when the band is playing ’cause its very loud.
All in all this is the perfect neighborhood hang out any night of the week (CLOSED ON MONDAYS, PEOPLE). There is no dress code and no expectations. Family owned and operated. Totally relaxed. Good eats, good drinks! Bring your friends!

I wasn’t sure what to think when I walked in. The place reminds me of Texas — not a bad thing! just not what I was expecting. Our food and wine were delicious, and we happened to catch a live music duo playing classic country. Good stuff. Looking forward to another visit.

The first time I experienced Riddle’s, I was just walking down the street with a friend and we randomly decided to get a drink. We were pleasantly surprised with live blues music and a great beer and wine selection. Since then, I’ve been a huge fan.
It’s a great place to chill with friends, or by yourself. There are no TVs – in fact, there’s an old broken-​down television that states «Kill you television!» I love it!
The food is also really good. Their pasta is excellent and they have a good fish selection. They also offer a lot of local items in their menu. My only complaint is that it’s a tad overpriced. I also recently had the orange-​apricot soup, and I thought it wasn’t tasty at all. Could just be my taste buds, though. This place is worth the visit.

Let’s do a quick survey… How many of you love to go out and have cocktails with friends and have noticed that by the end of the night when everyone is hungry the friend food/​burger/​whatever standard «bar» food the place sells just isn’t cutting it? Enter Riddles Penultimate, a great place in The Loop which remedies the above problem. Riddles Penultimate has both a great bar and great food (not just consistent bar food but really yummy, complex tastes). Their menu changes constantly (with a few staples) so be sure to try whatever they’re featuring that day. I also love the vegetarian options like the fresh daily veggies and the vegetable platter. Oh, but don’t worry, Riddles also serves those bar food staples (like burgers and fries) for those of us who still like the bar food but would like it taken up a notch.

There is nothing tricky about Riddle’s Penultimate Café and Wine Bar. Located right in the heart of the University City Loop, Riddles is a great place to go with a friend to sit back and enjoy and a couple of glasses of wine.
Each time that I have been to Riddle’s I have always ran into someone that I know. Like them, I’m enjoying myself, usually sitting in one of the booths along the wall with some friends chatting the night away. Sometimes they even have live music. If that’s the case, then most likely we are listening to the band and talking between songs because the front of the bar is a pretty small space so the noise can get a bit loud there, but that’s no problem.
Riddle’s has an awesome selection of drinks and the bartenders are always quick with your order no matter how crowded the place may be at the time. That is one of the many reasons that I look forward to going back there. Also the crowd is just in general a real friendly group of people to be around.
Riddle’s Penultimate Café and Wine Bar is a great place to spend an evening.