Manly Monday’s – Date Night Roundup

Manly Monday’s – Date Night Roundup

Inevitably my dinner/travel partner frequently happens to be my fiancé, Ben. The first Monday of each month I’ll roundup a few of his favorites for my ‘Manly Monday’ guide, whether it’s his favorite date night spots (ahem, Italian restaurants/Steakhouses) like today, craft beer go-to’s, grill specialties or scotch must-buys. Hopefully this will be a fun feature focused on some of his food & drink & possibly other specialities where I don’t have the same expertise!

Chicago is the quintessential steak & potatoes town, in my honest opinion. Aside from our addiction to Italian food, going out to a steakhouse is one of our go-to places for date night. Luckily Chicago has some of the best steakhouses in the country and there are tons of options. While Ben generally goes for the largest rib eye he can find, I alternate between filets and crab cakes to steak frites or fish depending on my mood. No visit to a steakhouse is complete without a dirty martini, maybe some red wine and an order of steak tartar, at least not in our book. Steakhouses lead the roster for Ben’s go-to haunts but Italian still make an appearance.

In keeping with the “Savage Six” theme, all of my lists will be in 6’s. Comment or send me a message if there is anywhere you love that we should add!

  1. Bavette’s
    • Ben surprised me with dinner here after I got a promotion at work and we had such a lovely evening. With its warm ambience, candles and jazz music in the background it serves for the perfect spot for a night on the town. You really cannot go wrong with anything on the menu, the baked goat cheese and steak tarar are amazing starters and they make a killer martini to kick off the night. The last time we were here I opted for the steak frites and Ben ordered the dry aged bone in ribeye. How that man can take down a 22 ounce steak will forever amaze me. Add the creamed spinach and truffle mac & cheese on the side if you are feeling extra indulgent! You’ll have to call or snag a reservation well in advance, so plan accordingly.
  2. Gibson’s
    • While certainly not the sexiest spot on this list, Gibson’s is such a classic establishment in Chicago. It’s the kind of steakhouse that comes around with a cart to show you the different cuts of meat and desserts. For some reason this little monologue on all of the different cuts makes me a bit anxious but it’s one of Ben’s favorite parts of the experience. Now that the weather has warmed up I’m hoping we can head back soon and people watch in the Gold Coast. If you’re feeling up to it, order a slice of the chocolate cake! Which I am pretty sure is nearly the size of an entire cake itself. We actually went here on our first ‘double date’ with Ben’s parents and it made for a nice atmosphere for our first time meeting!
  3. Maple & Ash
    • When it first opened back in 2016, Arch Digest ranked it one of the best new restaurants in Chicago. The space itself is gorgeous and it’s a fun excuse to get dressed up. Enjoy a cocktail before dinner at the bustling bar, or head straight to your table where immediately upon seating, they serve you with their ‘amuse booze’ aka a mini-serving of their cocktail of the day. They also bring you English radishes with salt and butter which I love. The menu has some serious hitters on it as well as some carefree appeal i.e. the line item “I don’t give a f*ck” where they order your entire meal on your behalf. While we haven’t splurged for that particular experience, you can’t go wrong with their steaks or scallops and I’d make sure to order the house made ricotta angnolotti if you have enough room in your appetite. I first brought Ben here for his birthday and the service did not disappoint. We happened to run into our friends who sent over champagne, and right then and there at our table our server taught Ben how to saber champagne. Luckily no one was injured in the process and it made for an unforgettable memory (not to mention one pretty outstanding party trick!)
  4. Gilt Bar
    • I must admit that long before I came around, this was one of Ben’s favorite go-to spots for dates. While I haven’t ever pressed for too many details, it’s a great set up with it’s beautiful, low lit atmosphere and an easy place to transition from drinks to dinner if the date is going well. Luckily for me Ben brought me for a whole meal of food (haha). The menu is solid , he loves ordering the steak tartar and orecchiette and I make sure to get the little gem salad (greens, avocado, radish & sherry vinaigrette), the ricotta gnochhi and a martini to get things started.  
  5. Picollo Sogno
    • I will admit 100% that if you paid me to tell you what to order off the menu, I would have no clue. We went here on our second date and I remember when he suggested it a few days after our first, I couldn’t help but get a little excited that maybe this guy was a keeper because it seemed like such a DATE NIGHT spot based on everything I heard. The outdoor patio is absolutely beautiful and romantic in its own special way apart from many other patios or al fresco dining one can find in Chicago. It truly feels like you’ve settled in to a restaurant in Italy, with its twinkling lights and ivy and the fact that they are serving up wine and pasta creates a winning combo in my book. I was so incredibly nervous for that date that true story I drank a beer in the back of my uber (sorry!) and was still shaking when I walked up. I couldn’t have been more pleased to see Ben looking handsome dressed in a jacket and jeans and nice shoes. A guy who loves Italian and picks solid date night spots and is well dressed? Sold. I may not remember what my meal consisted of (red wine, gnocchi?) but if you are looking for a exceptional spot for a dinnertime rendezvous, add this place to your list.  
  6. Monteverde
    • Ben adds this as the final spot to his list of favorites. I cannot recall exactly how we started our little tradition, but we leave work and immediately head here right after they open up their doors at 5P. We bunk up at the end of the bar, our favorite seats in the house and don’t bother putting our name in for a table. The bartenders are friendly & familiar to us and we enjoy watching the two women make fresh pasta behind the counter. As I shared in a previous post, one of the bartenders, Patric has become our buddy and recently shared this interesting article Food & Wine recently published on the restaurant’s unique culture – you can check it out here. Don’t come by without ordering the Burrata E Ham with prosciutto butter, the PBT! and/or sunchoke toast and the gnocchetti con pesto. You cannot go wrong with anything on the menu and if you’re looking for a day time date, you can now check out Monteverde for brunch! I’ve added the Ragu Alla Napolentana to our mental note of things to order during our next visit, my coworker swears by this dish namely for the leftovers it provides the next day for lunch or dinner.

So there you have it, this month’s manly Monday roundup. It’s my first go-around at this but I am thinking that perhaps next time, I have Ben take a stab at writing the post OR I can interview him so his voice comes through. What other topics are you interested in reading about from a man’s perspective? Always feel free to comment or email me,

Have a lovely week!



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