During a special celebrity edition of the show, Richard welcomed former A Place In The Sun host Amanda Lamb and Homes Under The Hammer presenter Martin Roberts as guest players.
In his opening speech, Richard singled out Martin, who also appeared on last year's I'm A Celebrity… Get Me Out Of Here!
The 46-year-old quiz god said: "Lovely to have you all here. I'm especially delighted to have Martin here. I've wanted him to come on for such a long time.
"The two great houses of BBC daytime television – Pointless and Homes Under The Hammer – finally, finally married."
Richard Osman made a naughty joke at Martin Roberts' expense on Pointless Celebrities tonight
Martin appeared on the teatime quiz show with former A Place In The Sun star Amanda Lamb
There is a semi in Barnsley
Evidently a big fan of the property series, which Martin, 53, presents, talk between Richard and his co-host Alexander Armstrong, 46, turned to their favourite moments from the show.
Richard said season three was a particular highlight for him, quipping: "No spoilers… but goodness me, there is a semi in Barnsley you want to see!"
Martin began to laugh as did the rest of the studio audience at the playful innuendo.
Richard singled out Martin for a special welcome as he is a fan of Homes Under The Hammer
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The best moments on BBC quiz show Pointless.
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Unfortunately for the property developer, his Pointless experience was relatively short-lived as he and Amanda, 44, crashed out in the first round.
Richard began the first questions on UK Geography by telling the guests: "If your job has been going round the country all the time for the past 13 years to different places, you should be rather good at this."
Failing to rise to the challenge, Amanda and Martin achieved the highest score of the round and were subsequently sent home.
Pointless continues on weekdays at 5.15pm on BBC One.