Seattle's work culture runs on sprint cycles, launch weeks and travel that can eat an entire month with almost no notice. A 2026 guide on reading Sugar Daddy schedules by industry notes that tech-industry men tend to be younger and more casual about timing than, say, surgeons or pharmaceutical executives with rigid calendars - but "casual" in tech usually still means booked solid on weekdays and only truly free in short bursts.
The practical move is to batch your first meetings instead of spreading them across the week. If your calendar only really opens on a Thursday evening or during a lighter sprint, say so directly rather than trying to force a Tuesday dinner that gets rescheduled twice. Members who state their real windows up front get further, faster, than members who agree to anything and then cancel.
It also helps to separate a first meeting from a commitment. A quiet dinner or a coffee near South Lake Union or Capitol Hill is enough to judge chemistry before either person names a monthly figure. Save the allowance or per-meet conversation for once you both know the arrangement is worth structuring.