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Assuming you save Tammy, she and Cal will naturally end up dating during Glow of year 15, and tell you about it on your following birthday (assuming one of them is your best friend) in Quiet 2 of year 16. If you want to prevent this in order to date one of them, there are two ways.
1) Keep Tammy's confidence low
You can select some dialogue options that will avoid making her more confident, and anything that you say to either of them to suggest that Cal might not like Tammy or could choose someone else will lower it further. If her confidence is low, then in Quiet 2 of year 16, Cal will show up and say he asked her out but she declined. This will leave him open to be romanced in year 18.
2) Flirt with Tammy to make Cal jealous, then confess to him
Early on in year 15, Cal can approach you and ask if you have feelings for Tammy. I'm not 100% certain on the requirements to get this scene, but I think just having Tammy's friendship isn't enough. I finally got it to happen on a run where I took every flirt option with her (and also Cal, since he was my real goal).
Once you get this scene, and assuming you have 80 friendship with him, you can confess to having feelings for him. If you do so, during your birthday in year 16, he'll tell you Tammy asked him out, but that he said no to keep his options open. This will also leave him open to romance.
Ooooh I see, it seems I'm doing the 1st option since most of my choices are lowering her confidence.
Maybe I'll do another playthrough with the 2nd option after this one. But thank you!