Right now the Sipping Point handles two broad classes of events pretty well. Drop-in events. The host is 100% going; they’re just advertising it. That’s a common, low-friction pattern: “I’ll be here, come if you want.” The classic Sipping Point event. You pick a specific time and place, then people can RSVP. That works when everyone is happy to commit to a fixed plan. But people don’t always plan like that. Sometimes they just want to hang out and they don’t care exactly when or exactly where. They need to find a time that suits most of the group, then find the right restaurant, pub, activity, or someone’s home. I’d like to support those kinds of events: get the conversation going, gather feedback on what times work best, then help them find the right venue. Or, alternatively, start with a specific idea (“Let’s try this new restaurant”) and then help pin down the right time. ...

The drop-in event was a success. After many traditional events with a minimum attendee threshold not succeeding, we had one that worked. Several friends dropped in, and I got to see some people I hadn’t hung out with in a while. It was a fun day. I wonder if the “anchor”—someone who is guaranteed to be there—lowered the bar for commitment. With a regular event, nobody wants to be the first to say yes, or the one who shows up when it might not happen. With a drop-in, you’re not committing to the event; you’re just deciding whether to swing by. Maybe that made it easier to say yes. ...

Sometimes you don’t want a big to-do. Sometimes you just want a low-key hang at the local pub or brewery. You might even go to those things alone, but it would be cool if someone you knew popped in. That’s what drop-in events are for. You advertise, with a little advance notice, something fun you’re going to do anyway, and you invite specific people to join. No pressure. You’re going regardless; it’d just be nice if a friend showed up. In the app, drop-in events have no minimum threshold of attendees. They’re effectively events with a threshold of 1: you’re going; anyone else is optional. ...

Groups in Sipping Point can now have owners and admins. That gives you a small set of people who can manage the group and, more importantly, control who sees the weekly event suggestions before they go out to everyone. Who gets the weekly suggestions The Concierge sends its weekly digest only to owners and admins. It is not sent directly to anyone else in the group. The idea is that admins and owners can look over the suggestions, do some curation or filtering on their own, and then forward the digest to the rest of the group—or choose not to forward it. So the rest of the group only sees what you’ve already vetted. ...

I’ve reworked the Groups section in Sipping Point into three clear areas: what’s coming up, how automatic suggestions work, and who’s in the group. The goal is to make it obvious how to set up automated events and to leave room for what we add next. 1. Upcoming events This is the docket for the group—everything that’s already on the calendar. Suggested events that have hit their RSVP threshold show up here as confirmed; others stay in the list until they trip or get cancelled. One place to see what the group is doing. ...

The Sipping Point still does what it did back in the day: people suggest events, send out invites, and if enough say yes, the event trips. We had some success with that—happy hours, trivia nights. Since bringing it back, I’ve been trying to expand on it by using LLMs to suggest events instead of having people create them manually. I’ve been at that for several months with mixed, mostly bad, success. The events that get suggested are not well received. ...

Before COVID, at my old job, we built an app called The Sipping Point. It was kind of like Kickstarter for happy hours: suggest an event (e.g., trivia night), pick a place and time, set a minimum number of people, then pass the invite around. If enough people said yes, the event was on. Otherwise it was cancelled. It was an easy way to plan events with minimum overhead. During COVID it stopped getting use. Then it got overrun with bots creating fake accounts, and Heroku severely increased their pricing. So I took it offline. ...