Happy Friday, gang! There’s a particular kind of magic that happens in December — when the fire is crackling, the lights are twinkling, and the evening calls for something warm in your hands. This week on Fridays with Oscar, we’re leaning into all of it with two recipes made for fireside entertaining: Oscar’s Hot Toddy and Bacon-Wrapped Dates stuffed with blue cheese and goat cheese. The Hot Toddy is named for our beloved Oscar, of course — a distinguished drink for our most distinguished gentleman. And the dates? They’re the kind of sweet-savory bite that disappears the moment you set them down. Together, they’re the perfect pair for cozy nights at home or intimate holiday gatherings.
Here’s What You’ll Find in Today’s Post
- 🥃 Oscar’s Hot Toddy — a warming bourbon cocktail with honey and star anise
- 🥓 Bacon-Wrapped Dates stuffed with blue cheese and goat cheese, drizzled with balsamic
- 💡 Comprehensive FAQs for both recipes with make-ahead tips
- 🛒 A Trader Joe’s shortcut that makes these dates a breeze
- 🐾 A check-in with Oscar & Ollie
- 👗 A look at what Beth and Kelly are wearing
Oscar’s Hot Toddy & Bacon-Wrapped Dates
Some recipes just feel like a hug — and this week’s pairing is exactly that. Oscar’s Hot Toddy wraps you in warmth from the first sip, with bourbon, honey, lemon, and the lovely licorice note of star anise. The Bacon-Wrapped Dates bring that irresistible combination of salty, sweet, and creamy that makes them impossible to eat just one. Best of all, both recipes come together quickly and can be prepped ahead, leaving you free to enjoy the fire — and the company.
🥃 Oscar’s Hot Toddy
If you’ve been following along with Fridays with Oscar, you know that our sweet German Shepherd is the heart of our home. Oscar is dignified, loyal, and has a certain quiet elegance about him — the kind of presence that commands a room without ever demanding attention. It only felt right to name this cocktail after him. The Hot Toddy is, after all, a distinguished drink: timeless, warming, and unfussy. Just like our boy.
This is my go-to drink when the temperatures drop, and I want something that feels like a hug in a mug. The combination of bourbon, honey, and lemon with those warm spices — cinnamon and star anise — fills the whole house with the most wonderful aroma. I like to use local wildflower honey, which adds a lovely floral note, but any good honey will do. It’s the kind of drink that makes you want to slow down, light a candle, and savor the season.
✨ Beth’s Tip: For a party-ready version, make a big batch in a slow cooker. Combine bourbon, honey, lemon juice, and water (scale up proportionally), add several star anise, and keep on the “warm” setting. Let guests ladle into mugs and add their own garnishes.
Frequently Asked Questions
Oscar’s Hot Toddy
Q: What type of bourbon works best for a Hot Toddy?
A: A smooth, mid-range bourbon with caramel and vanilla notes works beautifully — think Maker’s Mark, Buffalo Trace, or Woodford Reserve. You don’t need to use your fanciest bottle since it’s being mixed with other ingredients.
Q: Can I use a different spirit instead of bourbon?
A: Absolutely! Irish whiskey gives a smoother, lighter flavor, while scotch adds a smokier depth. Brandy is another classic choice. Use whatever you enjoy sipping.
Q: How important is the star anise?
A: The star anise adds a subtle, lovely licorice note that makes this Hot Toddy feel special. If you’re not a fan of that flavor, you can omit it or substitute a cinnamon stick and a few whole cloves.
Q: Can I make a batch ahead of time?
A: Yes! Mix the bourbon, honey, and lemon juice ahead and store at room temperature. When ready to serve, add hot water to each mug and garnish. For parties, use a slow cooker on the “warm” setting (see Beth’s tip in the recipe).
Q: What’s the best honey to use?
A: A good-quality local honey or wildflower honey adds wonderful flavor. Avoid ultra-processed honey if possible — the more flavorful the honey, the better your Toddy will taste.
Q: How do I keep it warm without overheating?
A: Use hot water that’s just off the boil — not actively boiling. Boiling water can make the drink taste slightly bitter and will evaporate the alcohol more quickly.
Q: Is a Hot Toddy actually good for a cold?
A: While we can’t make medical claims, there’s a reason Hot Toddies are a cold-weather classic! The warm liquid, honey, and lemon are soothing, and the steam can feel wonderful when you’re under the weather. Just drink responsibly.
Oscar’s Hot Toddy
Ingredients:
- 2 oz bourbon
- 1 tablespoon honey or to taste
- 3/4 oz fresh lemon juice
- 1 cup hot water
- 1 star anise
- Lemon wheel for garnish
- Cinnamon stick for garnish (optional)
Instructions:
- Warm your mug: Pour hot water into your serving mug to warm it, then discard.
- Add honey: Place honey in the bottom of the warmed mug.
- Add lemon juice and bourbon: Pour in the fresh lemon juice and bourbon.
- Top with hot water: Add hot (not boiling) water and stir gently until the honey dissolves.
- Add star anise: Drop in the star anise and let it steep for a minute or two to release its flavor.
- Garnish: Add a lemon wheel and cinnamon stick if desired.
- Serve immediately while warm and soothing.
Tips/Notes
Did you make this recipe?
We’d love to see! Tag us @styleatacertainage
🥓 Bacon-Wrapped Dates
I’ll be honest — these bacon-wrapped dates are the appetizer I make when I want people to think I spent way more time in the kitchen than I actually did. They look impressive, they taste incredible, and they come together in about 30 minutes. The secret is the combination of creamy goat and blue cheeses tucked inside each date, the salty crispness of the bacon, and that balsamic drizzle at the end. A little sprinkle of fresh thyme, and suddenly you have something that looks like it belongs on a restaurant menu. Trust me, these will disappear fast — make more than you think you need.
✨ Kelly’s Tip: Using pre-cooked bacon is an absolute game-changer here. It cuts the cooking time significantly, reduces mess, and still crisps up beautifully in the oven. Trader Joe’s fully cooked bacon is our go-to — it’s affordable, reliable, and makes this recipe truly effortless.
A Word About Shortcuts
When you’re entertaining during the holidays, anything that saves time without sacrificing flavor is worth its weight in gold. Trader Joe’s Pre-cooked bacon means no splattering, no grease cleanup, and no babysitting a pan. You simply wrap, bake, and serve. It crisps up perfectly in the oven and tastes just as delicious as the from-scratch version. This is the kind of smart shortcut that lets you enjoy your own party — and we’re here for it.
Frequently Asked Questions
Bacon-Wrapped Dates
Q: Can I make these ahead of time?
A: You can assemble the dates (stuffed and wrapped) up to a day ahead. Cover and refrigerate, then bake when ready to serve. They’re best served warm, straight from the oven.
Q: Can I use raw bacon instead of pre-cooked?
A: Yes, but you’ll need to adjust. Use thin-cut bacon, wrap tightly, and bake at 375°F for 25-30 minutes, turning halfway through, until the bacon is crispy. Pre-cooked bacon is much easier and faster.
Q: I don’t like blue cheese. What else can I use?
A: If blue cheese is too strong for you, use all goat cheese for a tangy, creamy filling. Cream cheese with a little honey is another delicious option, as is mascarpone.
Q: Can I add nuts to the filling?
A: Absolutely! A toasted almond or marcona almond tucked inside with the cheese adds wonderful crunch.
Q: What if I can’t find Medjool dates?
A: Medjool dates are larger and softer, making them easier to stuff, but Deglet Noor dates work too — they’re just smaller, so you may need to adjust the cheese amount.
Q: How do I keep the bacon from unwrapping?
A: Using toothpicks is key! Secure each wrapped date with a pick before baking, and they’ll hold together perfectly. Plus, the picks make for easy serving. Or swap out the toothpicks for reusable cocktail picks for an elegant presentation.
Q: Can I make these on the stovetop or air fryer?
A: An air fryer works great! Cook at 375°F for 8-10 minutes, checking halfway. Stovetop is trickier since you want even crisping, but a cast-iron skillet over medium heat can work in a pinch.
Q: What’s the best balsamic glaze to use?
A: Look for a thick, syrupy balsamic glaze (sometimes labeled “balsamic reduction” or “glaze”) in the vinegar aisle. Trader Joe’s, Whole Foods, and most grocery stores carry it. You can also make your own by simmering balsamic vinegar until it reduces by half.
Bacon-Wrapped Dates
Ingredients:
- 24 Medjool dates pitted
- 4 oz crumbled blue cheese
- 4 oz goat cheese softened
- 12 slices pre-cooked bacon such as Trader Joe’s, halved
- 2 tablespoons balsamic glaze for drizzling
- Fancy cocktail picks for serving
Instructions:
- Preheat oven: Heat oven to 400°F (200°C). Line a rimmed baking sheet with parchment paper or a silicone baking mat.
- Prep the dates: If your dates aren’t already pitted, use a small knife to slice them open lengthwise and remove the pit. Be careful not to cut all the way through.
- Mix the filling: In a small bowl, combine the crumbled blue cheese and softened goat cheese. Stir until blended (it’s okay if it’s a bit chunky).
- Stuff the dates: Spoon about 1 teaspoon of the cheese mixture into each date. Press gently to close.
- Wrap with bacon: Wrap each stuffed date with a half slice of pre-cooked bacon, securing with a cocktail pick.
- Arrange on baking sheet: Place wrapped dates seam-side down on the prepared baking sheet.
- Bake: Roast for 15-18 minutes, until the bacon is crispy and the dates are warmed through.
- Drizzle and serve: Transfer to a serving platter, drizzle with balsamic glaze, and serve warm.
Did you make this recipe?
We’d love to see! Tag us @styleatacertainage
🐾 Oscar & Ollie
Oscar has fully embraced the holiday spirit this year — he’s been supervising the cocktail-making from his favorite spot on the couch, looking very distinguished in his festive bandana. (He takes his role as official taste-tester seriously, though we draw the line at bourbon.) Meanwhile, Ollie has claimed her throne inside the Christmas tree, where she spends most of December batting at ornaments and giving us her best “I’m definitely not planning anything mischievous” face. Between Oscar’s couch lounging and Ollie’s tree-dwelling, we’re pretty sure they’ve got this whole cozy season thing figured out.
🔥 Beth’s Fireside Style
This bow sweater has been on heavy rotation since it arrived — it’s festive without being “Christmas sweater” territory, if you know what I mean. I love how the burgundy ribbon detail picks up the color of my burgundy riding boots, and layering it over a crisp white button-up gives it a bit of polish.
Shop Beth’s Fireside Look
The velveteen pants are pure comfort (with stretch!), and the ivory keeps the whole look soft and wintery. It’s the kind of outfit that takes me from puttering around the kitchen to answering the door when guests arrive — no outfit change required.
🔥 Kelly’s Fireside Style
I’m leaning into the cozy-chic vibe this week with the 2025 Rollneck Sweater in Stripe from J.Crew— it has that perfect chunky texture that feels festive without being overly holiday-themed. The black and ivory marled knit pairs beautifully with the Original Straight Corduroy Pants in dark green (from Gap Factory) for a sleek, modern silhouette.
Shop Kelly’s Fireside Look
I’ve finished the look with my Vans High Top Sneakers, which keep things casual and comfortable while still looking put-together. These sneakers are over 10 years old, but I found a similar version with the High Top Sneaker from Rothy’s. It’s the kind of outfit that works whether you’re hosting friends or running errands, and it captures that relaxed December energy perfectly.
🔥 Cheers to Cozy Season
As December unfolds, Kelly and I find ourselves craving these quiet, fireside moments more than ever. There’s something deeply comforting about a warm drink, a savory bite, and the soft glow of holiday lights. Oscar’s Hot Toddy and these Bacon-Wrapped Dates capture that feeling perfectly — they’re the kind of recipes that invite you to slow down, savor the season, and appreciate the warmth of home.
So light a fire, pour yourself a Toddy (raise a mug to Oscar while you’re at it), and enjoy a date or two. The holidays are meant to be savored.
🐾 Oscar, Ollie, Kelly, and I wish you a warm & cozy weekend!
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