Eight months in and still "complicated" sounds like the drawer where my ex and I used to stash random keys. If they can schedule trivia nights, they can schedule one low-stakes intro. I'd say yellow flag turning orange. A simple line works: "Pick one friend next week and I'll meet you both for coffee."
Separate vacations occur in about half of long-term couples with differing interests. Discuss boundaries upfront to avoid resentment. Balance with shared trips yearly. Budget solo ones affordably by choosing local destinations.