Kyou wa Kaisha Yasumimasu.

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Stories envolving a virgin in her thirties, with a boring looks, that met a guy who accepts them. Both leads loose their memories (not in the same way) so they cant remember If they did anything at all. Love Rerun is a bit sweeter because of the friendly and honest main guy. 

Very similar plots, but with very different art styles as one is 4-Koma. Older workaholic female lead mistakenly ends up sleeping with a younger co-worker, which develops into more than just an awkward drunken one night stand.  

Although Flower Garden it's a really short story, and KKY is a longer drama, the story is incredibly similar with an older woman that after a night of drinking, finds herself in the morning sharing the same bed with a younger guy and can't remember anything about what happened, at all. Flower Garden has a strange art, and cliches that Kyou wa Kaisha Yasumimasu doesn't, afortunately. But in general, these are the stories of older women, and their daily problems and worries in their brand new love-life with a very young, but mature guy. 

These two stories deal with an older woman and her encounters with a younger guy. Both stories represent very well their respective demographic. Toshiue no Hito is a lot more mature, and involves more mature situations (aka, sex scenes), the relationship between the main characters is a lot more sexual than you can expect it to be, and Kyou wa Kaisha deals more with romance and drama, the older woman and her worries regarding love-life. 

For fans of Kimi wa Pet, I suggest this new josei Kyou wa Kaisha Yasumimasu, like the former, we have a josei with an older woman / younger man set up and some similar issues with age gap. Their interactions are different though since the younger guy in Kyou wa Kaisha seems more mature than she does in some ways and there is less of the comedy to their interactions. The female lead is also less experienced in love. It is ongoing though so I don't know if the outcomes will be the same or not yet, we will have to see.  read more 

Although "Kyou wa kaisha Yasumimasu" is a long drama and "30-sai shojo OL" is only a short one-shot the main theme is very similar: A woman in her 30's who is still a virgin, desperately searching for experiencing her "first time" and falling in love with a younger (more experienced) man. 30-sai shojo OL is a little bit more smutty though.  

Although one is a four panel comedy, and the other a multipage drama, both in it's own way deal with the love and worries that occur when an woman in her 30s date a younger man in a May/December romance.