When and how did Dwight and Angela actually start their affair?

Question

In the office (US) Dwight and Angela had a secret at first relationship which was later revealed to the entire office. While they were shown to be greatly involved in their 'romance' it was never shown how and when did they actually start.

in S02E02 Sexual Harassment, Dwight reaches out Toby to ask some very awkward questions. Questions he would not have asked if had been involved with a women sexually. So I infer he wasn't at this point.

But then, in S02E08 Performance Review, Jim argues Dwight that You are not having sex. To which Dwight gives out a smirk as if he knows Jim is not true. I infer Dwight started with Angela by now.

And in the very next episode Email Surveillance, Dwight and Angela are at it in Jim's House party! So it is confirmed they are involved by now.

Considering Dwight's quirks and Angela such uptight personality traits, when and how did they actually start their affair? How did they even end up together! was it ever implied or inferred?

Answer 1

Dwight's character was expanded during the runtime of the show. Dwight's inexperience about female bodies is uncharacteristic of Dwight, who in later seasons is much more likely to be overconfident and compare humans to farm animals (which he does have extensive experience with).

S02E02 is quite early to establish Dwight's character, especially when you keep in mind that there was a dramatic shift between the first season and the second. This leads to small inconsistencies in character behavior, and I think Dwight's questions to Toby were indicative of early character traits which were changed later on when Dwight's character was expanded.

That being said, I think there are some reasonable arguments to be made.

• The show is a documentary, and we only see what the camera crew was interested in filming. The documentary starts with a strong focus on business, personal stories only get attention as the show progresses. Given the level of secrecy that Dwight and Angela use, it's very likely that the documentary makers didn't catch on until much later (when we did too).
• Angela is archetypically repressed. It's very likely that she doesn't really discuss women's matters in general, let alone with Dwight. Given Angela's strong religious tendencies and her generally repressed behavior, it's not too far-fetched to assume that she may not know everything about her body either (especially for previous generations, sex ed was often either lacking or absent).
• Dwight and Angela's affair may actually be the source (as opposed to the counterevidence) for Dwight's questions. Asking where the clitoris is would imply that Dwight is trying to sexually please a woman. Asking what vaginas look like may be a decoy question (to warrant the clitoris question without implying he's in a relationship) or the technical definitions he looked up confused him about the general layout of a vagina (he mentions "at the crest of the labia" which suggest he looked it up online).
• Dwight sucks up to Michael, who loves bullying Toby. Dwight may have been asking these questions purely to make Toby feel uncomfortable as a form of bullying (I do think this is less likely than the above, Dwight seems genuine in this scene)

None of this is confirmed, it's merely extending known character traits into somewhat logical consequences.