In The Big Inning...

Now that I've actually verbally told (or told people who would tell) all of the people who might find out about my engagement, I'm free to write about it. I figured that some of my friends might be offended if I didn't tell them in person and they had to read my blog in order to do so. At any rate, I can now tell the complete story of how it all occurred.

So, I'm sitting in a hotel room a few months ago, in Sumter, South Carolina. I'm down there for work, and it's only for a couple of days. I'm falling asleep, and for some reason it just comes to me that I want to marry Sam. I obviously am in love with her, and care for her very much, but hadn't really thought too much about marriage, figuring that there was really no rush. Apparently, it was just time, because that was really the first time I had seriously considered it.

It was kind of strange that the topic hadn't seriously come up before, but honestly, it really hadn't. Oh sure, nosy people had asked, "So, when are you guys going to get married?", and we had been together for a while (4 years this August), but I had always dismissed those questions for a couple of reasons. One was that I just found them annoying. The other was that I really thought it was a private decision, to be made by Sam and I together, and since we hadn't really discussed it, I wasn't too comfortable discussing it was others, even if they were close friends.

I did say that we hadn't really discussed marriage, and that really is the case. Some people find this strange, and to be honest, I do think it's a bit unusual. I don't think it was the case that neither of us wanted to jinx things. Rather, I believe that we were both happy with things as they were, and just enjoyed the time we got to spend together. I think we both figured we might get married, but didn't give it too much thought. This is unlikely the few other relationships I've been in before: In one, I was a silly young lad, and just assumed that I would be with my girlfriend forever. In others, I was more content to live in the present, whereas she wanted more of a long-term guarantee. While I do tend to plan ahead, I think it's important to try and "live in the now", which is why it was so refreshing to see that Sam was seemingly thinking the same way.

Once I had decided that I was going to strongly consider proposing to Sam, I did want to try and figured out if that was something she was ready for. However, Sam was more coy than I have her credit for. I did intend for my proposal to be a surprise, but I wanted to be as sure as possible that Sam would say yes. I tried to subtly bring up the topic - one time at a jewelry store, asking about what styles of rings she liked; another time just asking her how long she thought we'd be together. She may have known what I was up to, but that was kind of the point. But what Sam conveyed to me was kind of surprising: Basically, she wasn't going to tip her hand too much. The impression I got from her responses was that she really wanted it to be a surprise, and for me to put myself out there, by proposing. I hope that if she wasn't ready, she would have been more clear in her message, so as to avoid a catastrophe, but I guess we'll never know... At any rate, that only endeared me to her more: It was a nice, stark contrast from stories I'd heard (and even impressions from people I'd known) about girls who were constantly pushing to get married, in some cases just to assuage their own insecurities about their relationship.

So, I was mostly on my own for this one. I wasn't positive she'd say yes, but I was pretty sure. I decided to go for it. The next step was to get a ring. Up until this point, everything was mostly theoretical. I had researched engagement rings on the web, and had even read some proposal ideas, but had just files them away. They were intangible plans, anyways. Once I bought a ring, it made everything concrete. I could turn back (return the ring, or just keep it indefinitely) if I wanted to, but I knew that I wouldn't let myself. I waited about a month after I made my decision, and then decided to go for it. I took a day off of work (in mid-June), and made an appointment at Charleston Alexander. I had figured I'd spend most of the day driving around and shopping, possibly even going to Delaware (no sales tax!) if necessary. I wanted to do this right.

Up until this point, I had told virtually no one of my plans. The only serious discussion I'd had about the possibility of marrying Sam was back in January with one of my fraternity brothers. I had told him that I thought I might propose sometime in the next year or two, but was in no rush. Usually, I like to counsel my friends on important decisions. I'm pretty headstrong and like to make my own decisions, but I also respect my friends' opinions, and often look to them for support, because they're often insightful and see things in myself that I don't see. In this case, though, I decided that I was only going to tell one friend, and only because I would need her help in planning my proposal. I hadn't fully decided how I was going to propose, but I had a rough idea, and figured that telling one person would be reasonable. I chose to only tell one person because I really felt that one of the first people to know about my plans should be Sam herself, and not a ton of other people. I chose my friend Jenn Querijero, who I met after my senior year in college, when I worked as an intern at a marketing company in Boston called SIG. There were many reasons I chose to tell Jenn instead of anyone else: She was a great, trustworthy friend, was already married, lived in New York (where I planned to propose), and wasn't close friends with any of my other friends, thus reducing the likelihood that Sam, or anyone Sam knew, would find out.

So, on the way to buy the ring, I give Jenn a call. I tell her that what I'm going to tell her is something that she can't tell anyone else, and right away she knows that I'm planning on proposing. I just ask for the confirmation that I'm not crazy by doing this, which of course she provides. She was actually very helpful and reassuring. I go into the store, and start looking at diamonds. I had been planning on shopping around, but I either ran into the saleswoman of the year, or just got lucky. I was introduced to a senior saleslady named Dora, who was quite friendly, as one would expect. I told her that I had done some research online, but in truth, I was still intimidated by the whole endeavor. One thing that surprised me was that their prices were actually lower than what I had seen online. This set me at ease, because at least I was pretty sure that I wasn't going to get ripped off. But the clincher was when Dora actually tried to convince me that I didn't need to get a diamond of a better color, as the human eye really couldn't tell the difference between the one I was looking at an one that was a little worse in color, and therefore a bit cheaper. I told her that even though you might not be able to tell, I would know. She understood that (I mean, she wasn't going to twist my arm to get something cheaper), but I was impressed that she really hadn't been giving me the hard sell.

When I went in, I had in mind the price range I was going for, as well as size, color, cut, and clarity ranges that I was shooting for. I had anticipated shopping around, but Dora showed me a diamond that fit into all of the ranges I was expected, and I was essentially sold. She convinced me pretty easily to go for a platinum band. I found something that I though was simple and elegant, and selected it. I ended up very satisfied. It was probably one of the best "salesperson experiences" I've had. We even arranged to have her ship it to me at work in a couple of weeks, so that I wouldn't have to worry about losing it, AND so that I wouldn't have to pay sales tax, since she was sending it from Virginia to Maryland. Of course, relative to the price of the ring that was only 4.5%, but in the absolute, it was a pretty decent sum. I gave her my credit card, she rang up the deposit, and I was on my way. I left there very satisfied with what I had done, proud that I had selected a nice ring on (what felt like) my own terms, and excited for my future plans with Sam.

In truth, actually buying the ring was the easy part. Now I had to set my plans to propose into works. I really wanted it to be a surprise, and I thought that her birthday would be the perfect cover. I knew that I wanted to take her away for the weekend in order to propose, but if I did it out of nowhere, she would likely instantly suspect something, especially if the plans were as elaborate as I had been anticipating. But if I surprised her with a trip around her birthday, which was conveniently on a Friday this year (July 23rd), then she'd be less likely to think that something else was up. I was a bit worried about this - I didn't want her to think that somehow an engagement ring was her birthday present, and I didn't want her birthday to get lost in the shuffle. This ended up being much more of a concern of mine than it ever was hers - she's just not petty or materialistic at all, but I still wanted both events to be special for her.

So, the first question was where to go. My initial thought was Las Vegas. I know Vegas can be sleazy and crappy and low class, but it also can be fun and elegant and exciting. I hoped to take her to a great hotel (Bellagio, most likely), see a show, and just have a great time. I had thought that we might get a room overlooking the Bellagio fountains, and I would somehow propose when she opened the window to view the fountains, maybe with a sign on the window, behind the curtains. I hadn't really gotten too far along those lines.

Before I launched in the Vegas plans, I wanted to confirm that it would be a good idea. Sam's mother lives in Vegas, and she had mentioned before that it would be stressful to go to Vegas for fun, as she would feel guilty for not visiting her mother while she was there. I decided to email Sam's sister Tami, and ask her opinion. Of course, I wouldn't tell her about the proposal, just that I was going to take her somewhere for her birthday. Tami responded by confirming my suspicions: Sam likely would be stressed out by going to Vegas. Tami said that she knew that if it was her (Tami), she wouldn't enjoy herself as much. Tami suggested that I take Sam somewhere else, and save Vegas for some other time, possibly after their mom had moved from Vegas.

Tami provided some suggestions, including New York City, which I had been considering already. I figured that New York would be perfect because it had a lot of options, and it was close, which meant that we wouldn't be spending most of our weekend traveling. I pretty quickly settled on New York, and set about making plans. I still didn't know how I was going to propose, but thought that maybe I would still go with the window option. This, of course, depended on us having a hotel with a view: It would be kind of silly to somehow entice her to open up a window that faced a brick wall or a dumpster: Surprise, honey!

So, the first task was to find a nice hotel. This wasn't too tough in New York. In fact, the main challenge was to pare down the choices from the multitude of options. I searched for five-star hotels, and after about a week of internet research, I went with an "Urban Suite" in the W Times Square. They promised me that we would have a nice view, which seemed pretty reasonable, given that the hotel was in the heart of Times Square. They also had a nice "Sleep" package", which meant our room came with free sheets, cookies and milk one night, and a free CD. Done.

Next up: Travel. This one actually came to me pretty easily. I figured that flying to NYC would just be a pain, in general. I wanted the weekend to be relaxing and fun and laid back, and so I immediately thought that the train would be a better option. No waiting in long security lines, worrying about delays, parking at the airport, etc. The only problem was that I wanted the weekend to be classy, and historically, I haven't had what I would consider to be very "classy" train experiences. I've always thought that train stations are rather dirty, and that the trains themselves are quite grungy. Still, I thought that the Acela might be better. I looked online, and searched for Amtrak deals on Google, finally finding this site. It had a deal on there for Amtrak, and the first class prices weren't completely outrageous, so I took a gamble and went for it. In retrospect, this ended up being a fantastic decision.

Ok, ring, hotel, travel all taken care of. Next up: Plans. This was actually pretty easy as well. I looked on Ticketmaster and got us two tickets to see Avenue Q, which won the Best Musical Tony this year. I had heard good things, and I knew Sam likes comedies, so it seemed a pretty safe bet.

One of my other thought was that after I had proposed, Sam would likely want to tell someone in person, be it a friend or family member. First, I tried Tami, asking her if she was free to come down to NYC for Sam's birthday. She said it was unlikely, given that she was the Matron of Honor in her friend's wedding that weekend. I tried another good pair of friends, Dave and Laurel, but they were busy too. I then called Stephanie, one of Sam's closest friends from college. I had to sneak a peek at Sam's Palm Pilot to get her number. Sam and Steph are very close friends, but hadn't see each other in a long time. At any rate, I gave Steph a call, and she said that she would be very excited to come and surprise Sam, but that Sunday most likely wouldn't work - it would have to be Saturday. I knew that I wouldn't have proposed to Sam by Saturday, but figured that Steph coming was better than her not coming, so we figured out where we would meet.

As an interesting side note, Steph's boyfriend's name is Sam. When I called her, she picked up, and I said, "Hi, this is Dave Berman, Sam's boyfriend." Well, as she told me later, she was very confused, but just went along with it. I imagine she either thought it to be some kind of joke, or that she was about to learn something very revelatory about her boyfriend. At any rate, as the conversation continued, she quickly figured out what Sam I was referring to, but it's amusing nonetheless.

I had everything planned except for the most important detail: How I would actually propose. Even though I like the idea of having a sign on the window, it seemed that there were too many things that could go wrong. Maybe we wouldn't have a nice view. Maybe I wouldn't be able to get the sign in place without Sam noticing. There were just too many variables. I did like the idea of proposing AFTER we went to dinner and saw the show, but I also realized that might not be that possible. Another idea I had involved ordering room service and having them bring up a tray with dessert and the ring on it. But I also thought that was prone to error, and I didn't like the idea of anyone else having custody of the ring.

I finally decided that I would find a nice restaurant and propose at dinner. Yes, it would be before the show, but it would be romantic, and in an atmosphere I could largely control. I started out by doing a lot of research on the web, looking for 5-star restaurants in New York City. I read reviews that other people had given, looked for one that was in a reasonable location, and one that had a pre-theater dinner, since our show was at 8pm. I finally settled on a relatively small French restaurant called "La Grenouille", which had gotten rave reviews, was listed as highly romantic, had a strict dress code, and opened at the right time. I called them and made reservations, and told them that I was likely going to propose to my girlfriend at the dinner. They said that it was no problem; they handled stuff like that all the time.

At this point, I knew how I wanted to propose. I wanted it to be a surprise, and I wanted to be creative, but I didn't want to go through Rube Goldberg-ian machinations to do something contrived. I called up Jenn, and asked her to go to La Grenouille to scout it out and to see if she could snag a dessert menu. Of course, she was incredibly helpful and was willing to do whatever I asked. She went there, snagged a menu, and gave me a call. She said the place was incredibly romantic and would be perfect. I asked her to FedEx me the menu, and gave her my work address.

I received the menu the next day, and went to work. That night, after Sam went to sleep, I decided on the text of my proposal. I wrote what I thought was a simple and sweet proposal, of course ending it with "Samantha, Will You Marry Me?" I then printed it out, using some of Sam's nice resume paper. I cut the paper to the exact size of the menu, which was pretty simply designed - it was just two pages that folded closed like a book. Each side just had lighter paper attached to thicker paper, with the dessert items printed on the lighter paper. I cut my message to the proper size, and glued it to the lighter paper, half on one side, and half on the other. Unfortunately, the paper wasn't heavy enough, so the menu showed through. Eventually, I had to meticulously cut three sheets of blank paper for each side, and glued around the edges, so as to make it as flat as possible. Then, I affixed my proposal, and nothing showed through. It bowed out a little because of the glue, so I actually took an iron and tried to flatten it as much as possible. It looked pretty good when I was done, if I do say so myself. The whole time, as I was printing, and cutting, and gluing, and ironing, I was dreadfully afraid that Sam would wake up and find everything, but fortunately, she stayed asleep.

I FedEx'ed the menu back to Jenn the next day, and when she got it, she sent me an email that said, "I got it! *I* cried, and I'm not even Samantha!" She had asked me before if she could read it when it arrived, and of course I said it was fine. So it was nice to know that she found my proposal touching. I figured I had done a good job. The clincher, though, was when she told me that she brought the menu to the restaurant, and had given it to the Maitre'd with very specific (printed!) instructions attached. Apparently, there were a few middle-aged "New Yawk" ladies in the restaurant, and they overheard Jenn's conversation. One of them asked to see the menu, and when she read it, said to the others, "Oh my gawd! That is sooo romantic! You gawtta see this." One of them read it as well and said, "My husband is such an asshole! He proposed in Madison Square Garden." I think one started crying, and the Maitre'd had to console them. Jenn called me with this story, told me that everything was in good shape, and I was pretty confident it would go well.

Finally, the planning was done. I had the ring. I had the hotel and transportation. I had the dinner reservations, the theater tickets, and my diabolical plans in place. Everything was all set.

Obviously, things turned out pretty well, but I've written more than enough for one post, so I'll save the details of how things took place for another post.