No problem with any of that really. I'm thinking this is sort of going to be them "running into" (even if not actually in person) one another again after something that started then broke up before she found out she was pregnant.
I need to add the end to his relationship with Mason to his bio. That was at the end of June 2010 after Mason told him she was going to teach summer school in DC. Up until that point he at least held out hope that Mason would end up in Boston with him. No reason why he and Roxanna couldn't have at met before that though. He arrived in Boston in April 2010 and was in DC since June 2009 before that. Anything earlier you can see in the Career Chronology part of his bio.
I'm still thinking about how he finds out about the pregnancy. I'm initially leaning to her telling him. There's some interesting drama to him finding out, but the actual play of it might be a bit more difficult since there's only the two of them making the majority, if not all, of the story.
His AIM is CallsignTelly. I tend to have chat open through Meebo, although not necessarily have all my char accounts visible. If you sign on though and I'm available I'll pop him up.
As for the PB, no problem. In general, unless I really don't like the look, I'm pretty easy about my partner's. I really wouldn't have even known who Jenna was accept when we started talking I was kind of looking to see what else I could find for Channing icon-wise and saw her name. I started Telly with Ben Browder, but we changed games and the new one had a PB to char age match range that Ben couldn't fit. I'd happened to see some icons of Channing, where I thought they looked alike, and that's how I ended up with him. The only one of my PBs I really know all that much about his personal life is Jamie Bamber since he'd my favorite.