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There are hundreds of free flash dating sims.
Was it super cartoony? Anime style? Realistic? Were the characters animated or voiced at all? What kind of music played, if any at all? Was the first one set in a high school as well? Was this a serious dating sim or a parody? (Parody example: I remember playing a dating sim around 2011 where, no matter which choices you picked, you'd end up going out to dinner with a huge green orc.)
It was specifically a Nick game, though. Nick doesn't have that many dating sims.
I'm pretty sure the graphics were semi-realistic. The protagonist is a New Transfer Student, I believe. I remember it being serious. You could get a job, date other students, etc.

Does anyone know which games I'm thinking of? I'm having a hard time finding anything on them online. I remember them being Teen Nick (The N?) games circa 2008-2011.
One was a dating sim. I remember it being on The N's website.
The other was probably on The N as well. I remember you being able to create a character. It was a high school sim. You could date and other things. I don't think it was a MMO.