Remus Lupin and Molly Weasley
The first time that Molly Weasley and Remus Lupin had met was at a an impromptu parents evening, Dumbledore had reasoned that just because Remus wasn't employed anymore there was no reason not to let the parents know how their children had gotten on. This was especially true as Quirrell and Lockhart had been in no state to give feedback on performance in defence against the dark arts. She had been absolutely terrified. After finding out everything from Ron and the twins about the school year as she always did, she had been utterly horrified to discover that all year, her children had been taught by a werewolf. They were one of her biggest fears, and she spent the whole day before the meeting a bundle of nerves, not able to do anything. Once she actually arrived and met Remus Lupin, he could clearly see that she was nervous about meeting him and once more he felt ashamed of his condition. Still, they managed to get through the hour of talking about her children with minimal difficulty though the tension was there. Molly walked away feeling slightly reassured, yet still concerned that her children had been taught by a werewolf.
However, the second time that they met was under totally different circumstances. In Harry and Ron's fourth year, at the end of that awful tournament Harry was in the hospital wing, she had started to see him as one of her own now and she had to go and be with him. Remus Lupin was there too. It was okay this time though, because Harry needed him, and she would put up with just about anything to make her children happy…