Cocktail Conversations


Cuffing season is upon us, and we wanna help! We’re a social group for people like you who want to live life to the fullest and connect over brunch, cocktails and good vibes! Join us to meet new people, chat about dating and relationships in Portland.

Please note: You must be single and over 21 years of age to be a part of our activities.

Cuffing Season 2021

 It’s that time of the year! The weather starts to turn cold and singles are beginning to actively search for romantic partners in the hope of having someone with whom to ride out the colder, snowier, bleaker months. From mid-September through February. Scroll to see the cuffing season schedule!


Sept 15 - Oct 15

Now is also the time people are surveying the scene for last-minute flings.

Try Outs

Oct 16 - Nov 15

This phase is all about testing the waters to see if the person you claimed has what it takes to lock it down.


Nov 16 - Nov 30

You made it on the team but you are not officially playing yet. I call this the “situationship” phase. A situationship is when you are seeing someone casually without defining the relationship; you are not exactly sure what it is.

Cuffing Season

You did it! You are officially coupled up. You put in the work and it has paid off enormously.

Dec 1 - Jan 14


Jan 15 - Feb 12

The obstacles of dating are no match for you. You are a true warrior of love! Playoffs are the last leg of your journey before you are undeniably cuffed, lock and key, old faithful, whatever you want to call it.

Bae Day Weekend!

Congratulations! You survived the cuffing season and are on your way to a serious romantic relationship.

Feb 11-15

Feb 11, 2021, 4:00 PM – Feb 15, 2021, 11:00 AM
Kimpton Hotel Vintage Portland,
422 SW Broadway, Portland, OR 97205, USA
Can you make it?
No upcoming events at the moment