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When I just stare at her, she continues, “I just want to know if you are finally going to do something about it?”
“What?” I squeak. “Back up. What are you saying?”
“Lil, Oliver has always been the guy for you. Think about it: you have always compared all your boyfriends to him and found them lacking,” she continues. “And you’ve always been so funny about his girlfriends.”
“You have to admit they have all been pretty bad,” I interrupt.
“I know,” she agrees. And then she drops the bombshell. “And Oliver has always had a thing for you too.”
I lean forward, getting very close to Amy’s face, and say in a loud voice, “What are you talking about?”
Amy sighs. “For two seemingly intelligent people, you are pretty dumb about this.” When it looks like I am going to explode, she continues, “Haven’t you ever wondered why Oliver has hated every guy you have ever dated?”
“I never really thought about it,” I admit. “Generally, I end up hating every guy I date as well.”
Amy grins at me and nods in acknowledgment. “Well, Oliver has always been protective of you. Some may say almost possessively protective. Think about this: I am his sister, and he could not care less who I date. And he never comments about the love lives of Madi or Sammi,” she points out. “But with you, he has so many opinions, and none of them are positive.”
I think about what Amy is saying, and it is true, Oliver has always been pretty vocal when it comes to my love life and has left Amy and the girls to make some pretty poor decisions about their own.
“That just means he trusts your judgments more than he trusts mine,” I throw at her with a little triumphant jig.
“Maybe?” Amy replies, unconvinced. “But it is more than that. Take, for example, that time Seb broke up with you and left you up in the snow?” I nod for her to continue. “When I told Oliver what happened, he went berserk. He was worried and angry and had his keys ready and was in his car to get you before I could even get my shoes on.”
“Wait! I thought Oliver came for me because you couldn’t do it?”
“Lilly, Oliver didn’t give me a choice. As soon as he heard you were by yourself and upset, he couldn’t get to you fast enough. To make sure you were OK. It was very sweet, in an annoying way.”
I take a minute to ponder this new information in silence as I pour us both some more wine. Could Oliver have feelings for me? Feelings beyond the protective-big-brother type?
Another thought enters my head. “OK, well how about the fact that his girlfriends are always my polar opposite? He has a type, and it isn’t me!”
Amy shakes her head at me, disappointed. “That may be true. He does seem to gravitate to the well-organised but oh-so-boring girls. I have never been convinced that is who he wants to be with but more like who he thinks he should be with.”
As I think about this, Amy adds, “And what about you, Lilly? Have you dated people the same as Oliver? Or have they all been like Seb? From what I have observed over the years, you tend to go for guys that are nothing like Oliver.”
Stumped by this, I ask another question, “Why has he never asked me out?”
“Why haven’t you ever asked him out?” she throws the question back at me. “You are both too scared to make a move and face potential rejection. Or ruin your friendship. So you both do nothing, date the wrong people, and generally make everything miserable for me.”
“Sorry to make your life so terrible,” I say in a voice that contains no amount of remorse. “So it wouldn’t bother you if I was to be with Oliver?”
“Are you kidding me? You are already like my sister. This would just make it official,” she says, almost bouncing up and down with excitement at the thought.
I know I need to calm her down and get the conversation back on track, so I tell her, “Slow down, Ames. I’m still not convinced you are right and that Ollie has feelings for me.”
“But you are in love with him!” she repeats.
“I know,” I say. “And apparently, so does everyone. Gosh, I hope Oliver doesn’t know!” I add with a panicked look.
Amy gives me an adamant shake of her head. “No, he is just as clueless as you.”
Great. Thanks, I think to myself.
“Now I need to figure out where to go from here,” is what I say to Amy.
“You don’t need to make any big moves right now. The beauty of this pretend relationship weekend you have coming up is that you can just test the waters. See if Oliver responds. See what it would be like to be with him that way? It may all happen naturally, and then you will know.”
Once I agree this is in fact a good plan and that nothing more can be done about this now, I pack up some treats for Amy to take home to Oliver, give her a big hug filled with gratitude, and with Johnny as our escort, walk her to her car to say goodbye.
