$100 twice a week is spendy, but not rounding up to $70 is cheap. I don’t think $100/person for full meal + drinks + after drinks is a lot in a city, it’s more of the frequency that’s the problem.
If you want to go out with them and keep costs down, go less frequently, i.e. 1-3 times a month. Be the one to suggest the time so it’s either after work happy hour with drinks and apps or just after dinner drinks. And suggests cheaper places or places that are sit down, but where you order at the counter, like “fancy” food halls. (Chicago has several, where they are like food courts but way better because they are off shoots of legit restaurants.) Those are great to hang out but have non-awkward separate tabs. Same for bars actually. If you skip dinner or go afterwards to get drinks at a bar, you usually have separate tabs.
Also, if you are really only having one drink and a couple bites of an app, whilst everyone else has many drinks and lots of food, then when the bill comes just pitch in your fare share, generously rounded up and including tax and service charge/tip. That way you’re not being cheap because your overpaying your share, but you also save by paying much less than the overall per head amount. I.e you buy a $13 drink, throw in a $20. Have cash available to make it easier. I have a friend who just doesn’t drink much (and is mustachian). When our group goes out, she often only has one and then water or soda, while the rest of us have three and order apps. I’ve never thought it was cheap of her to throw in a $20 while we divide the remainder equally amongst ourselves. We usually all over pay, because we’re all rounding up and sometimes she ends up paying nothing, especially if drinks are like $5 happy hour. We give her $20 back or tell her not to put in anything, because it doesn’t make sense for her to do so if she had one $5 drink. It doesn’t bother me if I end up paying a whole $2 of her drink/tax/tip in that scenario and I don’t think she’s cheap.
