How can I reconnect with Tiffany and tell her what she means to me without feeling like I am making the possibility of losing her more real?

I love her, but I don't know how to tell her.

In high school, I cared deeply for a classmate and quietly helped her, but I never found the courage to speak to her, so she graduated without knowing that I liked her. I still imagine what I would do if I had the chance to meet her now.

Should I send one gentle message to check in, or would it be better to wait and give her space?

I had been dating a woman I met through an app, and we talked every day before and after meeting for dinner. After that meeting, she stopped replying for about a day, which is unusual for her; I am worried about her and also worried that she may have been disappointed or no longer interested.

How can I tell whether leaving is the right choice when I still care about her but feel that my efforts have not made the relationship feel close or mutual?

I have been trying hard to make my girlfriend happy for about a year, including spending money on gifts and activities, but I still feel lonely, shut out of parts of her life, and unsure that she really knows or wants to know me. I am now wondering whether I should leave.

How can I set a clear limit on how often or when I listen to her vent, while preserving our relationship and encouraging her to develop other ways of handling her emotions?

My sister frequently contacts me to process conflicts in her marriage, and I no longer have enough energy to provide emotional support at the current frequency. I still want to be supportive when I genuinely have the capacity, rather than cutting her off completely.