Rules in Wolverhampton, Sandwell and Walsall prevent households from mixing in pubs and restaurants due to a surge in cases leading them to be placed into the Government's Tier 2.
It has meant less trade, even on busy weekend nights, leaving many places struggling to stay open.
And bosses said even with those visiting for a bite to eat, it was almost impossible to check if they were living together.
Kim Langford, licensee of The Black Country Arms pub in Walsall, said it had been "stressful" and was like "jumping through hoops".
She said: "We've had to organise our tables so if we've got single people coming in, they can sit on their own and then you get potentially less people in the pub – it's really had an impact on trade.
"The weekend wasn't as bad as I expected but Friday was quiet. It's difficult, but all you can do is ask to see if people are in the same household and that's what we do.
"If they say 'yes' then that's as much as we can do – we can't ask them for their council tax bill, but we're asking and asking people to check in with the app.
"It's difficult and quite stressful because you think you've got a system set up and the parameters change again – it's the rule of six a few weeks back and it's changed since."
Ms Langford said trade had been returning to near normal levels in the lunchtime last month with people returning to the office, but it has since taken another blow due to people now being told to work from home.
She added: "It's stressful because I want to ensure I can completely follow the rules, but it seems to be you're jumping through so many hoops – one after the other.
"You're always thinking 'what's going to happen next? Will there be a complete lockdown?'"
She has, however, welcomed the latest round of support from Rishi Sunak, and said: "It's great news – it should really help us as trade is still down. It's encouraging and much needed.
"We have a few in, but it's the food trade we struggle with. We don't have the normal office workers coming in as they're at home. So it feels really quiet. We're about at 80 per cent on drinks trade but only 20 to 30 per cent on food.
"I did have to stand one of the junior staff down, so I've been filling in myself."
Bobby Basran, who owns the New Merridale pub in Wolverhampton, said: "I think all the Government regulations, from a pub perspective, become very difficult to manage.
"It's affected our resources – we've had to bring in extra staff – to make sure we adhere to the rules. But it becomes very difficult – how can you tell if someone is in a bubble?
"How can you check if they're lying about being part of the same household? We don't know and what can we do? It's becoming difficult because you can see people do want to go out and drink.
"And it's really had a significant impact on the footfall – a lot of people have been put off by the restrictions. Going out to the pub, it's not what it used to be.
"I think the Government is doing the best it can really, but this is going to have a material impact – not only in the weeks and months, but potentially years. There's no end to the virus in sight."
Mr Basran said it was a case of "changing times" but stressed he had seen tons of cars on the road at 10pm – when the pubs close – which he said was a sign people want to go out.
"There's this whole thing – you can't mix households and you've got the rule of six as well and more and more rules are coming in and it's having an impact on footfall."
Amrik Singh Saini, who runs The Fourways bar and grill in Rowley Regis, said it was difficult to manage and stressed people didn't like being asked if they belonged to the same household.
He said: "It's very hard to manage with the rules – it's very difficult and it's really had an impact. It's hard to manage social distancing and now people can't mix with households either.
"They can lie easily about it and we can't check their IDs and say they're not – because they say they're living together and you don't know what you can say or do.
"If six or a bunch of people show up we ask them 'you don't look like you're from the same household' and they say 'we live together, why are you asking?' and they don't like it. It's difficult but we're following the guidelines and doing what we can do."
Kim Degan, manager of The Tamebridge pub in Tipton, said the rules had been difficult to police – and stressed they hadn't been clear in the first place.
She said: "It's been difficult to monitor it. People are relying on others to use common sense but people forget and have some drinks.
"It's a nightmare to police because you're saying 'mask on' or 'move over' and 'you can't do that' and it's just a nightmare.
"The maximum number with the restrictions we can have in is about 25 – before all this madness it was 100, or 120, and it's a massive blow to us.
"We find ourselves phoning round other pubs – we're part of a chain – and asking what's happening. When we went into the tier system we didn't know what was happening.
"Nobody knew if the mixing households related to pubs, or whether it was just people's homes because they didn't specify really."