I’ve decided to make a concerted effort to share more Louisville-focused content, so when I shot this next to one of my favorite dinner date spots, Ostra, I figured it was the perfect excuse to share five of my favorite dinner date spots in town.

Date nights are one of those things I wish I did more often. And not just dates with Drew but dates with my girlfriends too. Nothing better than a delicious meal and a big glass of wine with friends. Extra bonus points for those super long dinners where you don’t want to get up from the table. It’s also a solid excuse to get a little more dressed up than normal. I feel like we do them less frequently in the summer, since there’s pool days, lake weekends, concerts, weddings and other random weekend activities. But now that fall is on the horizon, I’m itching for a nice dinner with friends, preferably al fresco (once the humidity dies down.

Pretty regularly I get asked about my favorite spots in town for _________ so I’m going to start doing round-ups of my recs every couple weeks. If you have any specifics you’re looking for, drop me a DM or comment below and I’ll add them to the list.

For a Special Occasion: Jack Fry’s

My favorite birthday/anniversary/special occasion spot is, hands down, Jack Fry’s. It’s a classic.

The atmosphere, even on a random Tuesday, is always great and has that big city feel that’s lacking in a lot of local restaurants. Not sure what it is – the piano player, the close proximity of the tables, the history – but it feels so different than other local spots.

And that’s before we get to the food. I’ve never had a bad meal at Jack Fry’s. The lamb lollipops may be my favorite meal in town and the pork chops are Drew’s go-to. Go hungry because you’ll probably want to get an appetizer – the shrimp and grits are so flavorful and rich – and dessert. If you’re celebrating, they usually bring you a special off-menu dessert – it’s a warm vanilla cake that is SO insanely good. It may be the reason why I normally go when we’re toasting to something special.

Reservations aren’t required but are highly encouraged (you can use OpenTable). That being said, you can always try to grab a seat at the bar to eat, drink and people watch.

For a Girl’s Night: Ostra

Ostra is relatively new, it opened last spring/summer, but has quickly become a favorite. Ostra is the newest restaurant from Chef Adam Burress, who is behind Louisville favorites Game, Hammerheads, and Migo. It’s tapas-style with a mix of seafood-focused and heartier South American-inspired dishes. I’m not a big fan of seafood so I can vouch that there are a lot of options that aren’t straight from the sea.

The menu changes pretty regularly but my favorites on the current menu include the chicken chorizo empanadas, the duck grilled cheese, the szechuan plantain tacos and the crispy brussels. It’s great for a girls night because, for some reason, I feel like it’s easier to order a ton of small plates and split them with girl friends. And if you want to eat outside, they have a patio big enough to accomodate a larger group (which is sometimes not the case).

If you go, plan on ordering a bunch of different options and sampling a little of each. I’d also encourage you to be a little adventurous since sometimes combinations that look strange on the menu pair really well. And make sure to order one of their spicy margaritas. They’re the perfect mix of tart, sweet and spicy… almost too perfect. Last time, I think I had three (hand to face).

Plus, after dinner you can walk next door to The Champagnery to keep the fun going.

Address: 1758 Frankfort Avenue 

For a Steak: Brendon’s Catch 23 

Okay, so I know I may get a lot of flack about not picking Jeff Ruby’s but I think Brendon’s Catch 23 has the best steaks in town. It’s known for their fresh seafood but since that’s not normally my bag, I always go for the steak. The first time I went, I wasn’t expecting the ‘melt-in-your-mouth’ deliciousness that came with my filet. I’m also a big fan of the rack of lamb and their strip steak.

Seafood lovers will be happy with everything else on the menu, especially since they fly in all their seafood fresh daily (that UPS hub coming in clutch). When it comes to sides, they all get my stamp of approval. My personal favorites are the mac and cheese and the haricots vert.

If you’re heading to a show or concert downtown, it’s a great spot to grab apps and drinks beforehand. Sit at the bar, enjoy some live music (they have jazz pretty regularly) and try their oysters or tuna tartare. For bigger groups, I’d recommend reservations – they also have private dining rooms –  but if it’s just a couple people, you can usually grab a table.

This is also a great spot for dinner if you have friends who are in-town and staying at one of the downtown hotels. It’s an easy walk or a quick scooter ride from almost any of them.

Address: 505 S. Fourth Street 

Anthropologie Snakeskin Skirt
(grabbed this one on sale; this one is super similar and cheaper – $42!)
Z Supply White Tee | Veja V10 Sneakers 

Low-Key Date Night: Mojitos or Havana Rumba 

You don’t want to get all dressed up or mess with parking. If you just want a good meal, a nice stiff drink and a little one-on-one time. Mojito’s is your spot. Havana Rumba, from the same ownership group, is a close second.

Both have seriously tasty margaritas and I’m a sucker for their sangria (they do a frozen version too). As someone who grew up in Miami, it also makes me feel at home. Their latin food is some of the most authentic in town – I could seriously eat the empanadas and croquettas all day. At Havana Rumba, I usually go for the Ropa Viejo with extra plantains. At Mojitos, since it’s a tapas menu, I like to go a little wild and other a few different things. Aside from the aforementioned empanadas, I love the chimichurri steak and the stuffed dates. But honestly, you can’t go wrong with anything. I’ve also heard really good things about their Paella but forewarning, it takes an hour so if you want it, order it as soon as you sit down.

Both are located in spots with ample parking (even if the lots are a little crowded); Havana Rumba has three locations (Highlands, Middletown and St. Matthews), so there’s one pretty close to everyone.  Mojitos does not take reservations but does have call ahead seating. So give them a call before heading out the door and you should be good to go by the time you arrive.

Address: Mojitos – 2231 Holiday Manor Center;

Havana Rumba – 4115 Oechsli Avenue 40207 (St. Matthews); 12003 Shelbyville Road 40243 (Middletown); 2210 Bardstown Rd 40205 (Highlands)

For a  Brunch Date: Butchertown Grocery 

Butchertown Grocery is delicious.

I’m probably partial to it since it’s RIGHT next door to my office but I could easily eat it for every meal of the day. I’d go broke and weigh a ton but I’d be poor, fat and happy.

My only complaint is, since the menu is seasonal, sometimes my favorite dishes come and go before I’ve had enough time to enjoy them. But that’s neither here nor there when it comes to brunch. Served daily, their brunch is different than your standard fare and always a little more elevated than the rest of the pack.

Their omelets are some of the richest and fluffiest around and always feature fresh, seasonal ingredients. And you’d be making a mistake if you didn’t try their seasonal muffin. The strawberry was my favorite and it tasted more like a cake than muffin… clearly no complaints here. The chicken + waffles is insanely good. The chicken is fried just right and the waffle is savory with rosemary and leeks baked in. My other favorites include the BLT and the chicken salad with housemade croissant. Oh and if the seasonal tomatoes are on the menu, order them. You can thank me later.

Reservations aren’t required but it doesn’t hurt to make them for brunch. I’d definitely recommend them for dinner but if you don’t, you can always get one of their craft cocktails or a glass of wine at the bar while you’re waiting.

Address: 1076 E. Washington Street (40206)

Photos by McKenzie Compton – Avistoria Photography