For a first time, this was pretty good. Very cute game. Dialogues could use a little work, but otherwise, it was fine.
I know this is just meant to be a short story, but I could see this becoming a much larger project. Guy comes back to his hometown and starts meeting his old buddies and of course girls from the past. His ex is already in there, so that could be expanded on (like why she is hooking you up with her coworker instead of trying to get back with you herself). As well, the whole business side of things as he did come here from his work to start on a new project. Pepper in a little drama and this has the potential for a really nice larger story.
Of course, a lot would need to be reworked and expanded on to fit that, but either way, what is here now is still good. A simple date story with a cute girl.
In the end, nice work for your first time. Interested to check out your next project. Best of luck and thanks.