Jen Rubin - A Decent Proposal

 

So, it took me climbing a glacier to get a new perspective on life. I don't know if it was the altitude or what, but it suddenly occurred to me that my life sucked. I wasn't doing the work I wanted to do. I was still in the Midwest. I hadn't managed to get back to New York City. I hadn't had a relationship that lasted longer than a few months. Maybe it was the altitude, I don't know, but it became clear to me suddenly that the problem was that I was just too passive, that I didn't take any risks and that from this day forward, I was going to be spontaneous. 

 

So, I got back home and I told my friends this, I was pretty excited about the new plan, and they said, “You can't actually plan to be spontaneous.” [audience laughter] Do you misunderstand the word?” But I knew I was onto something and it was going to happen. 

 

So, fast forward a little while, I started dating someone. We were together, I don't know, six months, nine months. We were in the kind of cagey stage of a relationship where, “I don't know how I feel about you. How do you feel about me?” kind of thing. “I don't know about moving with you to New York,” that kind of thing. And so, I was getting stuck in inertia, and I had spent many years inertia and I was hoping not to spend more time there. 

 

I went out for drinks with one of my very practical friends. I was having one of those evenings you can have in your 20s where you dissect your life in excruciating detail, every inch of it. As we were talking, she said to me, and Ruth was a problem solver, and I was not a problem solver, she said, “It sounds to me like you should just propose to Matt.” Matt was my boyfriend. 

 

I thought about it for a minute, and I realized the only relationships I had managed to sustain for longer than four months were the unrequited ones that I had been in. I was looking to not have a longer relationship that was requited. And so, I thought about it and I said, “You know, that's a great idea, because that really sounds like something a spontaneous person would do. [audience laughter] So, I am going to propose.” 

 

And so, by the time I got home, I was pretty sure I wasn't going to propose anymore. But I walked in the door, and my housemate handed me the phone. It was Ruth, my practical friend. And she said, “So, what's your plan?” And I said, “Well, I don't really have a plan.” And she said, “Okay, what are you doing Saturday night?” And I said, “Well, actually, as luck would have it, I'm going to the movies, so I can't propose.” And she said, “Well, what are you doing Friday night?” And she got me, because I had no plans. [audience laughter] I said, “I'm going to propose to Matt.” 

 

I hung up the phone, and I quickly called Matt before I chickened out and I said, “Pick me up on Friday. Look good,” and called an Italian restaurant in town, made a reservation. And then, it occurred to me that I had only four days to prepare. 

 

So, on Monday, I tried on every outfit in my closet until I found the one that I look best in. Tuesday, I drove through a snowstorm to get the engagement leather jacket, because I figured I had to give him something. [audience laughter] And then, on Wednesday, I developed my fail-safe plan, because I really hoped that with this new perspective on life, I was going to be bold while I did this bold thing, proposing. But I also knew myself, and if only one thing went wrong, I would be completely derailed. I would probably say something so self-effacing he would have no idea that I proposed. 

 

So, I made sort of like a Burma-Shave on index cards. And on each index card, I wrote one thing I loved about him, color coded. And then, on the last one, it said therefore… 

And that would be my cue to propose. I really hoped I wouldn't use this. I really hoped I'd be bolder than that, but it just made me feel good knowing that it was tucked away in the leather jacket box. 

 

So then, Thursday-- What did I do, Thursday? Oh, Thursday, I thought about every possible answer he could give me. I thought there were nine. [audience laughter] And so, I wrote out answer for each one. And then, on Friday, I took the day off of work and I rented romantic comedies to get in the mood. [audience laughter] And then, I realized I couldn't just stick the leather jacket in my purse, so I went and dropped it off early at the restaurant and I said, “Could you bring this out with dessert?” And they said, “Sure. What's the occasion?” And so, I said, “Well, it's his birthday,” which some of you are smarter than I was at the time, because I thought, well, what if he said no and then I'd be embarrassed in front of total strangers. So, that's what I did. 

 

So, anyhow, fast forward to the meal and it's clear something is a little off because I'm not eating. And then, they come for dessert and they ask what we want for dessert. And Matt, in an unprecedented move, said, “I'm full and I don't want dessert.” And so, I in also an unprecedented mood, because I usually eat all the bread at restaurants, I said, “Actually, I want dessert. We must have dessert.” 

 

So, Matt goes and excuses himself, because he doesn't know what's about to happen, but he knows something's about to happen. So, the dessert comes out. There's, , as you can imagine, the candle on the pie, and they're singing Happy Birthday, and it's one of those restaurants where all the waitstaff sings Happy Birthday [audience laughter] and the whole restaurant sing Happy Birthday. Matt's just saying it's not my birthday. I'm making eye contact with nobody. [audience laughter] And then, they leave and then Matt looks at me and I pull out the index cards in defeat and I hand it to him and I'm like, “Just read it.” 

 

So, he reads each card. He gets to the therefore… I do rise to the occasion and I do ask him if he will marry me and he does say yes right away, which is lovely. But I can't really leave it there, because the problem is that I hadn't told my instinct about my new perspective. My instinct has screwed me my whole life. And so, I said, “Are you sure? [audience laughter] Don't you need a little time to think about it?” Because that was what I thought he would say, but he was sure and he didn't need any time. Thank you.