Summer Session is from "Tycoon Games," but Hanako's logo is on it too, and it sure looks (and plays) like Georgina Okerson's work -- so, since there aren't any in-game credits, I'm going to assume it's hers. (Okerson also created Summer Schoolgirls, Cute Knight and Fatal Hearts.) In fact, Summer Session plays a lot like Summer Schoolgirls, redeveloped for boys. The objective here isn't to make friends, however, but to get a girl friend -- perhaps a minor difference, but one that adds a mild sexual frisson.
Summer Session is like Summer Schoolgirls as well, in that gameplay mostly involves choosing how to spend your free time -- working out, shopping, studying, etc. You have a limited number of options, and one open slot each weekday afternoon, with more time to spend on weekends. Actions affect your stats -- so studying increases your smarts, working out your hunkiness, and shopping the quality of your clothing, all things that may help you with some girls. Some activities may cause you to encounter one of the characters and learn more of their backstory -- and also give you a conversational choice that may make them think better or worse of you.
In other words, it's a simple resource management game bolted onto a fairly bushy narrative tree, with nice anime-inspired graphics for visual appeal, and a dating theme. From a design perspective, the theme -- and the omission of puzzles -- is the main differentiator from Summer Schoolgirls. As always with Okerson's games, though, it's nicely polished for what it is -- and because the narrative tree is quite bushy, it's a game you're likely to replay several times, to explore different outcomes and figure out what actions will help you land the different girls in the game. Which is good, because a single playthrough is pretty quick, so replayability is essential.
Rethinking
You remark on "redeveloping" the game in terms of a male viewpoint, but given that the original games of this type had a male viewpoint (all the way back to Tokimeki Memorial), I would say it's more like going back to the genre's roots...
Perhaps the author was only able to originally create these games from her own female viewpoint, and now she has the experience to replace her own viewpoint with a different one...
History
I'm vaguely aware that this genre has been common in Japan, but it seems quite rare in the west - I've seen the likes of SimGirl and so forth on Newgrounds, and they seem a lot more focused on the resource management aspect than the dialogue trees - as do the more commercial Western life management games such as the Sims and Kudos. I was thinking at the time that the closest a Western game has come to this kind of structure was the old Alter Ego, but if I remember correctly the encounters/decision points in that were a lot more linear and less bushy than this game seems to be.