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I've been that asshole. Though I was young and stupid and didn't initiate, I let it happen. Of course I knew better, but I let her acceptance and my dick run with things. They later divorced. I can't say she wasn't on her way out before I arrived but either way I'll never know. It's a bad thing for one's closet.
Considering your attempts a test of that relationship's strength is bullshit. Rationalization. Repeat that a couple times.
Surely you know by now that relationships and their stability aren't static. Even the best couples go through ups and downs. Being around someone for work, school, whatever, and maintaining a friendly demeanor is one thing. Discovering that person's status the next. If you know their status yet continue prodding, possibly in a time of weakness, and cause further damage then yes, you're an asshole. If you fail you just look like an idiot. Nice choice.
Steer clear, make note of the qualities, and keep looking. It's a big ocean.
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There are a vast number of people who are uninformed and heavily propagandized, but fundamentally decent. The propaganda that inundates them is effective when unchallenged, but much of it goes only skin deep. If they can be brought to raise questions and apply their decent instincts and basic intelligence, many people quickly escape the confines of the doctrinal system and are willing to do something to help others who are really suffering and oppressed." -Manufacturing Consent: Noam Chomsky and the Media, p. 195
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