Calla,
Your situation reminds me a little bit of my own experience with recuitment. I too was a junior transfer with an older boyfriend who was not very supportive of my interest in Greek Life. I'm also going to suggest you go through with recruitment. To address a couple of your concerns:
Even if you ultimately decide a sorority isn't for you, recruitment can be a great way to meet people. Also, I wouldn't worry too much about things being weird with women you already know from other organizations. Assuming you get along with these women already, your involvement in other groups on campus will make you a more attractive PNM and give you common ground to talk about during the parties (thus making it less potentially awkward, rather than moreso). And, I would hope that if recruitment didn't work out for you, the women you know from other involvement would be mature enough not to make things uncomfortable for you afterwards. Without knowing them personally, or where you go to school, this is just an assumption though.
As far as your pledge sisters being younger than you, it's all a matter of attitude. I was lucky that I transferred to a school with deferred recruitment so my pledge class was composed of other juniors & sophomores. Even so, I still became very close with younger women who were initiated after me.
Finally, a non supportive boyfriend can be a challenge. However, once my bf saw how happy Theta Phi made me, he slowly began to come around. Hopefully yours would do the same.
Good luck with whatever you decide! If you're interested I posted my recruitment story here. It's the only thread I've started, so it shouldn't be too hard to find
-J
ps, love your name
