Glen O'Brien was the man Dorothy has an affair with in Season 1. He reappears after his divorce in Season 5.
1986[]
Glen was the Gym Teacher at a School Dorothy was working at, she managed to speak to him after pushing in front of several students, they arrange a date soon after Dorothy in the glow of love. After several dates they checked into a Motel and made love, afterwards she and him are getting dressed and clearly they are happy with each-other and Dorothy passionately says that they go to a hotel and not leave or maybe dinner.
Glen then reveals the truth, he's married unhappily, Dorothy is angered that he lied, he admits he stayed for the children who he truly loved, if they had divorced his wife would have taken the children across State which would have broken his heart and while now his children are adults now, he can't bring himself to end it now. Dorothy in anger ends it, despite Glen pleading for her not to. Afterwards Dorothy is depressed unable to work and Glen calls her asking to see her again, however she turns him down only once Blanche and Rose leaves, she secretly calls him to see him again.
That night, Dorothy returns exposing her guilty truth to Blanche and Rose, she and Glen had dinner but clearly Dorothy was scared they were seen then they went to a motel. After a few dates despite Dorothy's enjoyment Sophia's warning finally works. That final date, Glen has to leave earlier, but Dorothy finally breaks up with him for good, she realises he's comfortable with being with his wife and having this second life of pleasure but Dorothy can't be the other woman and so while he begs her not to Dorothy says goodbye.
1990[]
Glen was divorced during the time between appearances, once it was finalised he called up Dorothy to see her again, within their first meeting they ended up back in bed and dating. Glen meets Sophia and gifts her a Cannoli revealing that despite his Irish name, he grew up with Italians. However he then proposes, but while Dorothy is unsure before, Glen's now ex-wife calls and Dorothy realises he's scared of being alone and needs to recover from the divorce before they could be together however Dorothy offers him friendship instead which he accepts.