Between work, kids, laundry, appointments and the mysterious ability of an entire week to disappear in roughly six minutes, date night can become “We should really do something sometime.” 😂

Consider this your sign to actually put it on the calendar.

For September, we're mixing cheap dates, romantic dinners, comedy, speakeasies, live entertainment, fall adventures and stay-at-home nights, with options from Colorado Springs to Castle Rock and Pueblo.

Prices below are approximate for two people unless otherwise noted and can change depending on food, drinks, tickets and gratuity.

🍸 Speakeasies & Secret-ish Spots

5

🥃 District Elleven | Colorado Springs
💰 Approx. $35–$75 for two
A moody 1920s Prohibition-inspired cocktail bar downtown. Dim lighting, whiskey, cocktails and an intimate atmosphere make this a great grown-up escape.

🗝️ The Archives Underground Libations | Colorado Springs
💰 Approx. $35–$70 for two
Head downstairs inside Colorado Craft for an underground cocktail date. This is a particularly good pick when you want drinks somewhere quiet enough to actually talk.

🎲 The Fifty-Niner | Colorado Springs
💰 Approx. $35–$70 for two
This one gets a ⭐ from me because it's not just another bar. It's a hidden speakeasy + board-game café where you reserve a two-hour table, choose a game, sip and play.

🥃 Shame & Regret | Colorado Springs
💰 Approx. $30–$70 for two
Hidden back-alley entrance, Victorian/gothic styling and a serious whiskey and Scotch selection. They also list Monday Scotch flights and late-night specials.

🍹 Allusion Cocktail Bar (Downtown) | Colorado Springs
💰 Approx. $40–$100 for two
This 21+ spot changes themes, making it one you can revisit and get a different experience.

🔐 The Vault Speakeasy | Colorado Springs
💰 Approx. $25–$50 for two
Hidden behind The Loft Music Venue with a 1920s-inspired atmosphere. Current listed hours are Friday and Saturday evenings.

🍸 Provision | Castle Rock
💰 Approx. $50–$100 for two
Dark, cozy and speakeasy-esque with craft cocktails and small plates. Perfect for the “we're wearing actual nice clothes tonight” date.

🔒 The Clink | Pueblo
💰 Approx. $30–$70 for two
This may be my favorite Pueblo wildcard. It's a cocktail/wine lounge in Pueblo's former city jail/police station, with live music on some nights. That's a date you remember.

😂 Laugh Together

September has some genuinely good comedy options.

Peak Improv Theater | Colorado Springs
🎟️ Many shows around $10–$15/person
💰 Date estimate: $20–$30 before dinner

September's schedule includes Stick Horses, Improv Colorado, Whimsicult, Tune Titans, Dead Puppet's Society and other shows.

See Peak Improv's September shows

Don't Tell Comedy | Colorado Springs
📅 September 5 & September 19
🎟️ $27/person
📍 Exact location is revealed later.

This is a fun twist on comedy night because you buy tickets knowing the general area, but not the exact venue or lineup.

Loonees Comedy Corner | Colorado Springs
September currently includes Mike Hammock Sept. 4–5, Moms Unhinged Sept. 10, Steve Hofstetter Sept. 14 and Louis Johnson Sept. 18–19, among others. Tickets vary by show, with several listed from about $12 upward.

🎶 Music, Entertainment & Something Different

🎵 Lulu's Downtown | Colorado Springs

September currently includes trivia Sept. 3, Ward Davis Sept. 8 and Colby Acuff Sept. 10, with additional live entertainment throughout the venue's calendar.

See Lulu's upcoming shows

🎷 Sinners & Saints | Castle Rock
💰 Approx. $30–$70 for two

Inside Ecclesia Market, this cocktail lounge promotes Friday live music and Saturday DJ nights, with bands and jazz also appearing in its programming.

🎸 Brues Alehouse Brewing Co. + Riverwalk | Pueblo
💰 Approx. $35–$70 for two

Have dinner or drinks, catch live music when scheduled and then walk along the Pueblo Riverwalk. Simple, relaxed and doesn't require an elaborate plan.

🍽️ September Restaurant Specials

Here's where I found an especially good September deal.

🫕 Melting Pot Customer Appreciation

📅 Every Sunday–Tuesday in September
💰 $49 per person
🍽️ Four-course meal
📌 Reservations required; mention Customer Appreciation when booking.

That's about $98 for two before drinks, tax and tip, but considerably less than a typical full Melting Pot date.

💕 Thursdate

Every Thursday, Melting Pot also has its romantic four-course dinner for two promotion.

👯 Fondue Girl Dinner

📅 Every Thursday in September
💰 $35/person
Includes cheese fondue, charcuterie and chocolate fondue, with $10 cocktails/drink specials.

That one works beautifully for our girls' night content too.

💰 DATE NIGHT UNDER $50

This absolutely deserves its own Buzzy section because date night should not require refinancing the minivan. 😂

🍦 Shake + Sunset
Grab dessert or milkshakes and find a scenic sunset spot. $15–$30

🎭 Peak Improv
Two $15 tickets + inexpensive dessert afterward. About $40–$50 depending on what you order.

🌮 Pueblo Riverwalk Date
Walk the Riverwalk, split an appetizer or casual dinner and grab dessert. $25–$50

🍂 Fall Picnic
Grab sandwiches, drinks and dessert and head to a park with a blanket. $20–$35

📚 Bookstore Challenge
Give each person $10–$15 to choose a book for the other. Grab a treat afterward. $30–$45

🎲 Thrift-Store Date Challenge
Each person gets $10 to find the funniest, weirdest or best item for the other. $20 + food

🥾 Hike + Treat
Pick a beautiful local trail, then go somewhere for ice cream afterward. FREE–$25

🌅 Coffee... Except Make It Something Better 😉
Skip the coffee and grab iced tea, smoothies or another favorite drink, then take a scenic drive. $10–$25

🎨 Dollar-Store Art Challenge
Each person gets $10 to buy supplies, then you have 30 minutes to create a masterpiece. $20–$30

🍕 Pizza + Game Night
Pick up pizza and buy a ridiculous card or board game neither of you has played. $30–$50

🏠 Stay-at-Home Date Nights

Babysitter unavailable? Bank account giving you the side-eye? Staying home still counts. 💗

🍝 Mystery Ingredient Night: Each person chooses one surprise ingredient and you have to create dinner using both.

🎬 Bad Movie Night: Find a spectacularly terrible movie, make popcorn and score it on acting, plot, costumes and “WHAT IS EVEN HAPPENING?”

🍷 At-Home Tasting Night: Cheese, chocolate, sparkling drinks, mocktails or other favorites. Cover the labels and rate everything.

🎨 Paint Each Other: Two inexpensive canvases. Thirty minutes. Paint your partner's portrait. Absolutely no artistic talent allowed.

🃏 First-Date Questions 2.0: Write questions on slips of paper ranging from ridiculous to meaningful and take turns drawing.

🍕 Make-Your-Own Pizza Competition: Each person gets half. Winner receives bragging rights and control of the remote.

🕯️ No-Electricity Night: Phones away, candles or battery lights on, cards and conversation. Pretend the Wi-Fi doesn't exist.

🧺 Living-Room Picnic: Blanket, finger foods, music and dessert. No dining table allowed.

📸 Memory Lane: Go through old photos and choose your ten favorite memories together.

✈️ $1,000 Fantasy Vacation: Each person gets an imaginary $1,000 budget and 20 minutes to plan a getaway. Compare plans afterward.

🍂 A Few September-Only Dates

🎈 Labor Day Lift Off | Sept. 5–7
Admission to Memorial Park is FREE, making an early-morning balloon launch + breakfast afterward a surprisingly good date.

🍸 Cocktails & Canapés Walking Tour | Sept. 26
📍 Downtown Colorado Springs
⏰ 4–6:30 PM

Four signature cocktails at four locations, appetizer pairings, Prohibition stories, a stop at one of Chef Brother Luck's restaurants and an exclusive speakeasy visit. This one practically has DATE NIGHT stamped across its forehead.

Cocktails & Canapés details and registration

🌶️ Pueblo Chile & Frijoles Festival | Sept. 18–20
Make it a Pueblo date: food, live entertainment, vendors and, naturally, a frankly unreasonable quantity of chiles. 🌶️😂

🎶 FREE 90s Concert | Sept. 17
📍 Philip S. Miller Park, Castle Rock
⏰ 6:30–9 PM
💰 FREE

Tunes for Trails/Perks for Parks features Ninety Percent 90s. Bring money for food/drinks and you've got a very inexpensive outdoor date.

💗 Buzzy's Date-Night Rule

Date night doesn't have to mean $150 dinner + babysitter + fancy clothes.

Sometimes it's cocktails behind a hidden door. Sometimes it's laughing at improv. Sometimes it's wandering a fall festival sharing something covered in green chile. And sometimes it's putting the kids to bed, ordering pizza and sitting on the living-room floor playing cards.

The important part is intentionally making a little time for the two of you.

Because before there were permission slips, grocery lists, practices, appointments and someone asking “What's for dinner?”...

there was you two. 💗🐝

I’d turn this into a standing monthly Buzzy Date Night Guide, with a fresh section of that month's concerts, comedy, restaurant specials, seasonal dates and under-$50 picks each month.