Cougar Date: Women 50+ & Men Under 50, South Norwalk, CT at Jacob’s Pickles

Cougar Date Night: Women 50+ & Men 50 & Under 💋🔥

Older, bolder, and ready to mingle.

Confident women 50+ meet curious younger men (25–50) for a one-of-a-kind night that flips the script on traditional dating norms. Cougar Date Night is where experience meets energy—and sparks just might fly.

Forget the apps and swiping fatigue. This is a real-life connection event built for bold women and the men who admire them. Whether you're craving conversation, chemistry, or just a damn good time, this one’s for you.

🍺 Pre-Game Mixer: Ease in with a drink (not included, but encouraged) and some casual mingling before the rounds begin.

💋 Mini Dates, Big Energy: You'll pair off for a series of quick-fire convos, with a cheeky icebreaker to keep things playful.

🔁 Rotate, Repeat, Spark: When the bell rings, you're off to your next match. Who knows what (or who) is waiting next?

✔️ Pick Your Match: After each round, mark “friend,” “date,” or “none.” Mutual matches get contact info the next day!

This event is designed for women 50+ and men 25–50. While these ranges help us create great balance, we won’t turn you away if you’re slightly outside the box and think you'd vibe with this crew.

🎟 Spots are limited and this one will sell fast—especially for women! Ladies, get on the waitlist early. Gents, don’t hesitate—your dream date might just be looking for someone exactly like you.

📲 Follow us on Instagram & Facebook @sipsandsparks for sneak peeks and secret promo codes.

Age Guidelines & Inclusivity

The age range for this event is a general recommendation. We welcome all participants regardless of age or gender and do not verify this information at check-in.We do not perform background checks on participants, so please exercise your own judgment when meeting new people, just as you would on any dating platform.Our goal is to create a welcoming and enjoyable environment for everyone.

Gender Balance & Attendance Disclaimer

We work hard to maintain a balanced ratio of male and female attendees by carefully managing ticket releases. However, we cannot guarantee exact gender ratios at the event, as last-minute no-shows are beyond our control.

No refunds will be issued due to uneven gender balance.

To reduce no-shows, we have a three-strike policy — anyone who misses three events without notice may be banned from attending future events.

We believe a positive mindset goes a long way — your experience is what you make of it, and many guests have a great time regardless of the final numbers.

Event Changes & Cancellations

We reserve the right to postpone or cancel events with insufficient registrations.If this happens, you'll receive either a full refund or the option to transfer your ticket to another event.

Waitlist Information

When events sell out, join our waitlist through Eventbrite.You'll receive an email notification when spots become available and can then secure your ticket through our Eventbrite page.

Important: Tickets must be purchased through Eventbrite only. We do not accept payment at the venue on event day.

Accessibility Notice

Some venues may not have elevators or full accessibility features.If you need specific accommodations, please contact us at before purchasing your ticket so we can confirm availability at that location.

Safety & Liability

By attending, you agree that participation is at your own risk.You release Sips and Sparks LLC, our team, venues, and partners from liability for any accidents, injuries, or damages that may occur during or after the event, including from interactions with other participants.

Photography & Social Media

We may take photos and videos during events for promotional purposes.By attending, you consent to being photographed and having your image used in our marketing materials.

Don't want to be in photos? Simply let our event host know when you arrive, and we'll make sure to respect your privacy.

Refund Policy1+ week before event: Full refund guaranteed (minus Eventbrite processing fees).For refunds, email us at .

Info: Check in to find your seat, name tag, and pull up the match sheet we'll be using throughout the event. Enjoy free mingling during this time to break the ice and get to know other attendees!

Info: Use the restroom, grab water, purchase drinks or snacks, stretch, and free-mingle!

Know what’s Happening Next — before everyone else does.

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