I think they might, but it will turn out to be a bad dream.

Not gonna happen. It was the big tease through season 1, followed up by the great twist ending when they woke up with other people (Moss and Moss' therapist respectively) after a night of drinking together. Graham Linehan, the show's creator has stated that he doesn't want them to hook up, citing what having Sam and Diane as a couple did to the dynamic tension on cheers. Plus anyone who has ever worked in IT or AV knows the last person you want to hook up with is one of your own. The last thing you want to share with someone you love is an appreciation of Ethernet cables.

Noooooooooo....! 'Twould ruin a good thing.

No. It's too funny the way it is.

I wish but they probably won't. I hope they continue to bicker with the flirty undertones though.

Bearing in mind that I have not seen Season 3 of the show yet so I don’t know what has happened in those six episodes, here are my thoughts:
Yes, I would put them together, but I think with all good writing, timing and patience would be of the essence and the writer/writers would need to work hard and long in deciding what season to make it happen in. I don’t want to see them make it happen too quickly but I wouldn’t want them to act too slowly and miss their opportunity, because that can happen in television land too. Personally, I would like to see them take one entire season to set it up. I would love to see a triangle with Douglas, Jen and Roy that comes to a head where Roy is put in the position to have to fight for Jen because I don’t think his character has ever really had to fight for anything of import. I also think it is imperative that Moss’ one night stand with Jen has to come out and freak out Roy and challenge him, even if it is very matter of fact to Moss. And I would love to see the season right after it built all about Jen and Roy keeping their relationship a secret from everyone…even the audience… until the very last episode to provide lots of nice hints and innuendos. And man, the scene where they do get together, if they do, better be as good as that scene between Moss and Roy and the police cars. I’m not F’ing kidding.

leave them just the way they are. funnier that way