Work / personal life dilemma

Difficult one, firstly the ‘friends’, you say that they are potential troublemakers, so don’t go on holiday with them, get your big girls pants on and tell them . No.

Secondly, maybe the sacking and ‘redundancy’ were something that compromised the Company and your DHs boss is aware of this and doesn’t want your DH involved?
He might be trying to warn your DH to stay away from them for his benefit rather than the Companys’.?
Can your DH afford to lose the contract because you go out with people that you don’t appear to like very much?
However, you are correct in that the boss shouldn’t dictate what you do on your time off.
As I said, a difficult one.

I think they can be troublemakers at work - if they don't get their own way.

The sacking involved a pay off so that he didn't disclose information he had found out about another colleague - who later resigned.

I think the boss dislikes the couple intensely because of the trouble they caused at work. He had to sort out the fall out from it. The couple can no longer damage the company but my DH worries that he will be 'damaged' by association.

My DH is worried that by associating with them he could lose his contract. However, we can't really say this to the couple. It is my DH's main income.

Is it really worth it to continue the friendship that you don’t seem overly bothered about. Imagine if your livelihood was seriously compromised by continuing with this relationship - could this friendship survive?

It sounds awkward, but I think your husband’s work must take priority. As others have said, you don’t sound overly fond of the couple really.

Don’t agree to holiday with them, and gradually reduce contact with them.

We had one such “friend”….keep away

I can fully sympathise with the “boss” you don’t know what has gone on before and there is a saying that you can judge a person by the company they keep..

Your husband depends on the boss of a business for a good work contract, but this boss appears to be attempting to control his relationships outside work, over which he has no authority whatsoever. over. A former colleague was sacked on 'suspicion ' of theft, his wife made redundant later, and there appears to have been a pay-off to buy someone's silence. All highly suspicious.
You know this couple and must form your own opinion of the possibility of them causing trouble. It would be foolish to jeopardise your livelihood but I would be very careful with the boss also; he has dealt with these people and removed them from his business so what does he fear?
Tread very carefully round all of them and keep your social life private.

I’d steer clear, neither you nor your husband know exactly what happened at the company, the boss does.

Calendargirl

It sounds awkward, but I think your husband’s work must take priority. As others have said, you don’t sound overly fond of the couple really.

Don’t agree to holiday with them, and gradually reduce contact with them.

I agree Calendargirl definitely don't agree to the holiday PinkCosmos

You don't need to be bosom buddies with the boss either, just maintain a friendly contact.