I'm talking about synastry, so the Pluto person would be the one who represents Pluto in the aspect.
Specific examples from personal experiences: I've known somebody who seemed very interested in me for a while. Whenever they'd see me in public they'd sort of follow me a long for a while and try to keep a conversation going for as long as they could. They'd ask me to hang out often, but I'd usually make up some excuse not to because I could see where things were going and I wasn't interested. I can be a bit passive aggressive. Even though, in this situation I was the Pluto person, and he was the Venus. Our two planets were at a trine to each other. Months went on like this, eventually I got a boyfriend, but Venus (although, acting very Plutonic) still persisted. Our "friendship" or whatever pretty much ended the day when he walked me home after seeing me out and about, stopped with me and forced me into a kiss. So, it's weird that the Planetary roles seemed to have been reversed. Especially since his Venus is in Pisces, a fairly passive sign, and my Pluto is in Scorpio.
I had a very similar experience with another guy whose Sun trined my Pluto. I was pretty interested in him, but I wouldn't say obsessive. On the other hand, I got letters from him in the mail (he had a Gemini moon) at least twice a week and usually they had a obsessive overtone, always talking about being together.
Again, with someone else I have been Pluto, but this is the circumstance where I actually feel like Pluto. I have been obsessed, borderline stalker to this person for the few years I have known him. His Venus trines my Pluto. And definitely find him attractive on multiple levels. We also have Moon conjunct Pluto. And when I get around him for a long time, I get so fixated on him it almost annoys me because I wish I could think about something else. I get the feeling that I scare the beejezus out of him because he keeps himself at a distance. Then again, he is a Scorpio moon and I think that might just be his nature.
But I've been thinking about this more since I posted this and I've come to think that perhaps with strong Pluto aspects it shows the potential for a strong connection to go either way, mutual or one sided. The way that each individual feels could depend on their relation to Pluto in their own natal chart, or the other planets involved in the two people's synastry.
So, I think I just answered my own inquiry?