My T is 10 years older than me so she understands things like sexuality and gender issues, which is important to me. She also understands the pressures of college, whereas an older therapist (like 50s or 60s+) probably wouldn't since college was much different for them than it is for me.
As for how we connect, we are both very funny and have similar senses of humor. We spend most of our sessions being goofy and laughing, which sounds counterproductive or odd for therapy sessions about serious topics, but it works well for me