Boff has unsuccessfully sought to become the Conservative candidate for Mayor of London on six occasions, most recently failing to gain the nomination for the 2024 election.

Boff finished once again in second place with 35% of first round votes, an increase of 31 percentage points on his run for the nomination in 2015 for the 2016 election.

Boff was placed first on the Conservative top-up list for the London Assembly in 2008, comfortably winning a seat.

In September 2015, Boff called for a managed street prostitution zone to be set up in East London in order to protect sex workers from harm.

It excluded Boff owing to the council's confusion over whether the statements he made about the cost of the mayoralty were legally admissible.

[7] By the time they decided that they were, it was too late to print, and the council compounded the problem by telling voters who enquired that Boff was not running.

[11] On 3 October 2023, Boff was swiftly marched out of the Conservative Party Conference by police after vocally expressing his disapproval of a speech by Home Secretary Suella Braverman, which he reportedly referred to as a "homophobic rant" and "tripe".

He has stated that his 2005 same-sex civil partnership was "register number 000001",[16] although it was not the first finalised because the 15-day waiting period was waived for a terminally ill man in Worthing.

[17] Boff is a libertarian,[18] and an outspoken proponent of direct democracy, having prominently publicised the issue at London mayoral hustings and on ConservativeHome.

On 10 June 2019, Boff ran into a burning tower block in Barking Riverside to help people escape a fire that had broken out.