Where in the Pacific Northwest should I ask her to marry me?

July 14, 2011 12:06 PM

Next week, my girlfriend (fiance, soon!) and I are driving from Oakland up to Portland and I'm going to ask her to marry me. She knows this already, but doesn't know when or where along the trip. So, I'm wondering if you local yokels can give me some ideas about when to go for it.

Our plan right now is:

Monday morning (early): Drive via I-5 to Umpqua National Forest. There's gorgeous waterfalls and this seems like the time to pop the question.
Tues: Chilling in hot springs and hiking/biking around forest.
Wed: Driving to Portlandia. We're staying at Kennedy School.
Thurs: Hanging out in Portland. We're switching hotels to Crystal hotel.
Fri: Chill in Portland, then heading out to the coast, driving south on 101. Finding a beach to camp at.
Sat-Mon: Just leisurely making our way back home, driving and camping along the coast.

My current plan is to ask her at the waterfalls on Monday or Tuesday and then we'll have the days in Portland in the hotel to... *ahem* However, I am thinking that building up the suspense and asking her later-- on the way back down the 101, might also be cool. But that contradicts the fact that I'm just anxious as hell to put this ring on her finger. :)

Any suggestions on how to make this more romantic and special for her? We're not "picture people", but I'll probably be asking strangers to snap some shots of us, so pretty scenery would be great.

Also, cool Norcal, Portland, and Oregon suggestions on what to do/where to eat are appreciated!

posted by jstef to Travel & Transportation (29 answers total)

If you are already going to Umpqua NF, then go to Crater Lake.
posted by Mister Fabulous at 12:12 PM on July 14, 2011 [2 favorites]

Next week, my girlfriend (fiance, soon!) and I are driving from Oakland up to Portland and I'm going to ask her to marry me. She knows this already, but doesn't know when or where along the trip.

Any suggestions on how to make this more romantic and special for her?

Did you like sit down with her and tell her that you're going to ask her to marry you during the trip? Because I feel that if you were wanting to make it more romantic or special for her, you should have not talked with her about it prior, and instead completely surprised her with a proposal during the trip.
posted by Dominic. Allen at 12:15 PM on July 14, 2011

Best answer: Well... what sounds better,

Anticipation or Celebration?
Anxiety or Joy?

(What sounds better for the hotel room, *ahem*.)
posted by carsonb at 12:17 PM on July 14, 2011 [1 favorite]

In favor of doing it on the way up, that is. Sorry no recs for where.
posted by carsonb at 12:18 PM on July 14, 2011 [1 favorite]

I think the waterfall idea is romantic and is overall a better plan, since the coast can be unpredictable. I was at the coast on the 4th of July and it was so windy that it was really miserable to be on the beach -- not exactly the perfect atmosphere for such an important moment!
posted by rabbitrabbit at 12:19 PM on July 14, 2011

Crater lake, or somewhere up the columbia river gorge?
posted by iamabot at 12:20 PM on July 14, 2011

Best answer: Oh man, if she already knows it's coming, then you could have fun with it and get some little presents to give her along the way. Things like cute little earrings, buttons, candies, flowers, whatever. Then she really won't know when you'll pop the question.

You say
1. darling/my love/honey bunny/sweetie/pumpkin / 3tc. etc. etc.
2. You're the love of my life/you're so very special to me/I adore you so very much / I want us to have moments like this forever / etc. etc. etc.
3. And so I have something for you / I want you to know how much you mean to me / I wanted to give you this / here's a little something / etc. etc. etc.
4. and give her the tiny present

And then you can just choose your moment along the way when you think is a perfect moment, after the first couple of times of course The ring in one pocket, your next "gag" gift in the other. And then afterwards, you can let her have the others at your discretion.
posted by lizbunny at 12:20 PM on July 14, 2011 [6 favorites]

Since the goal is to make it romantic and special, I might suggest being a bit more spontaneous about it. Since you're anxious to do it, just go for it when you're feeling like the moment is romantic.

As for how, I think the key is letting your love for her and the emotion of the moment come through. Only you know how best to do that. Maybe it's screaming "I love this woman" at the top of your lungs in a deserted valley. Perhaps it's evoking tradition and getting down on a knee or delivering a short speech. But, unless you have reason to worry you'll freeze up in the moment, I'd go for spontaneity. Since she already knows you're proposing on this trip, it may be the only spontaneous aspect of the proposal.
posted by maxim0512 at 12:21 PM on July 14, 2011

if everyone knows it's coming, do it early on the trip. people start acting weird during that limbo of almost, but not quite engaged. shorten that and enjoy all the *ahem* ing.
posted by nadawi at 12:23 PM on July 14, 2011

Print out a Google maps set of driving instructions, and make her the navigator. Somewhere down in the list of turns, hack in: "will you marry me?"
posted by StickyCarpet at 12:25 PM on July 14, 2011 [2 favorites]

Response by poster: Did you like sit down with her and tell her that you're going to ask her to marry you during the trip?

It came up during a recent, heated argument about getting engaged (ARE YOU EVER GOING TO DO THIS????), and I felt pretty stupid for giving away the surprise, after the fact. It was an easy out and I was pretty ashamed, so THANKS FOR THE SNARK! (Just kidding)

So now, I'm trying to maximize the surprise and specialness. Hence, the question. But since we're headed to some of the coolest geography and funnest cities in the US, IMHO, I'm trying to work that in.

Thanks for the suggestions thus far! I'm psyched about Crater Lake! I just read about the Old Man and now I get to see it. I also really like "fooling her" a few times and I'll probably fuck with her head a tiny bit. :)
posted by jstef at 12:28 PM on July 14, 2011

For a romantic dinner near the Kennedy School, I'd recommend either Autentica or DOC. Both are just a few blocks west of the Kennedy School. I'd recommend not eating at the Kennedy School, except for maybe breakfast. For a great coffee shop, check out Extracto, which is also right around NE 30th and Killingsworth.

If, by Wednesday, you haven't popped the question and need any help with setting something up, memail me. I live a block from the Kennedy School.
posted by perhapses at 12:31 PM on July 14, 2011 [1 favorite]

If you aren't sick of beautiful places by the time you get to Portland, take a drive up Larch Mountain Road to the top. On a clear day you can see 5-6 mountains including one of the best views of Mt. Hood I know of (other than from the top of Hood). Here's the directions.
posted by Mister Fabulous at 12:40 PM on July 14, 2011 [1 favorite]

If you want to do it on the way down, Russian Gulch State Park would be a pretty unbeatable setting.
posted by juliapangolin at 12:44 PM on July 14, 2011 [1 favorite]

Put the ring in her favorite snack (I'm thinking like a bag of chips), have it waiting in the car for her. She gets proposed to when she finds the ring!
posted by JacksonandFinch at 12:57 PM on July 14, 2011 [1 favorite]

Best answer: Nooooo, don't build up the surprise by waiting until you're on your way home to ask her, silly! If she knows you're going to propose, she might already be expecting it with this trip. Then, when you have the trip and don't ask her, she's going to be disappointed. There might be some tension that you don't want. When you do: great. Relief and all that. But there will possibly be some "Why did you wait?!" annoyance, and then how will you celebrate?! You already had most of your trip!

So, at the very least, hint about it along the way. Let her know something special's coming and then pop the question in Portland. Don't wait any longer than that.
posted by katillathehun at 12:57 PM on July 14, 2011 [1 favorite]

Response by poster: Okay, I'm probably going to go with my gut and ask her at Umpqua, in front of the falls, but on the SECOND day. I'll take her to some of the smaller falls and give her a cute gift at a few of them to build the suspense, and then we'll go to one of the big falls and I'll ask her (so thanks Lizbunny!)

Upon reflecting, I think you all who said to go for it early are right. Spending time with my anxious girlfriend is less fun than spending time with my ecstatic fiance! I'll be hitting up DOC (she loves Italian) in Portland.

Thanks!
posted by jstef at 2:08 PM on July 14, 2011

The Portland Rose Garden, on a sunny day, would be a nice place to propose, with Mt. Hood hovering over the skyline and all the roses in bloom. . .
posted by Danf at 2:10 PM on July 14, 2011

If she knows that you're planning to propose on this trip (as you say she does) and the subject has been the source of heated arguments (such as the one that caused the reveal), I appreciate your desire to make it special and as much as a surprise as possible... but a) propose early in the trip (Umpqua Falls of Crater Lake both sound good), and b) do not, for god's sake, do not try to fake her out with "psych! LOL!" proposals.

In fact, (in view of your comment on preview) I personally would suggest avoiding the 'cute gift to build suspense'-- if she's likely to be anxiously awaiting this, what makes you think she's going to take your 'cute gesture' correctly, rather than a consolation event because you've changed your mind? If she's strung up to expect something and this has been a source of tension, there is a non-zero chance you'll end up with a girlfriend who's angry/humiliated/disappointed by your 'gesture'. Sure, you might make up for it when you propose for real, but why one earth put her (and yourself) through a horrible evening (or even ten minutes!) just for the sake of a surprise?

Just propose, be sincere, and enjoy having your ecstatic fiance on a lovely vacation.
posted by Kpele at 2:17 PM on July 14, 2011 [2 favorites]

But there will possibly be some "Why did you wait?!" annoyance

On one end of the spectrum: do the build-up about something special happening at some point on the trip. Belabor the car packing, with champagne in an ice cooler, other seemingly portentous props.

Then, when pulling out of the driveway to start the trip, pull immediately to the nearest curb, put it in park, and ask.

"Well alright then, let's have a great trip now."
posted by StickyCarpet at 2:25 PM on July 14, 2011 [5 favorites]

i agree with Kpele - i think the build up, cutesy, psych type of gifts have more chances to back fire. she's already frustrated. she wishes it hadn't gone this far. she probably feels silly for the argument. she wonders if you really were going to propose or are saying it now to save face.

you can even ask her while you guys are packing - that would be unexpected and spontaneous - "Susie, i can't go another minute not being your fiance and i don't want to spend a second of this trip as your boyfriend, will you marry me?" then, go to the lake as planned and have the entire set up as if it were the proposal and do another little speech - "this is where i planned to do it, and i still wanted you to have the special moment. i love you"
posted by nadawi at 2:50 PM on July 14, 2011

Response by poster: Hrm... The two sides of the coin. I really think she's the type to like the cute gifts, especially if they are sincere. She LOVES handwritten notes and thoughtful gestures.

The fight wasn't all that major, it was just how I let it slip that I was going to do it, so I wouldn't read too much into that. We have a pretty playful relationship and there have been a ton of moments in the past couple of months where we were out on some rocky cliffs early in the morning or laying in the tent late at night and she said, "You should just ask me right now." But I didn't have the ring! So I think I can play into that a little bit! :) But I appreciate the caution and I will go about it in a really safe and respectful way-- I don't want to roller-coaster her emotions too much!
posted by jstef at 3:21 PM on July 14, 2011

I would play up the playful part of it then, since it seems like she's REALLY been pushing for getting proposed to. It's a little retaliation on your part for her being so pushy, and a little "letting her really savor it" too.

You could start off the trip with one of these pseudo-proposals, and when she kind of gets irritated at that point and hounds you for the real ring (again) then you tell her "nope, not yet. I promise you, that between now and the end of the trip, you will get your wish. But if I'm going to propose to you, I will do it how I want, and I will find the perfect moment for it."

Do the ridiculous proposals, like get down on one knee (maybe not the first time, be nice, that's intense), keep the presents in little jewelry boxes, do whatever you like. And then you've got the "nope, it wasn't perfect. Close, but not quite" retort if she makes noise. Tell her to relax, and enjoy it :)
posted by lizbunny at 4:06 PM on July 14, 2011

It sounds like she really, really wants to be engaged, and I'd be careful with the fake-outs; if she's at the point where this is coming up in fights, that might be enough to actually upset her, which is the last thing you want. Even if you're generally playful together, this is clearly becoming something she's emotional about. The "you should ask me right now" moments seem silly and affectionate, but the idea of a ring box with something else inside is less charming because you know it's going to be disappointing.

Why not propose early (waterfalls! yes!) and then continue surprising her with tiny gifts in ring boxes all weekend? That's silly and funny without the potential emotional drain of an ongoing is-he-or-isn't-he cycle. Then you get to have a joke that lasts all weekend while you're both already happy and secure in the relationship. You could go down on one knee in every restaurant and scenic place all weekend, and have a new (jokey or thoughtful or both) present at each. That could make her laugh and make her feel loved, but without adding any stress.
posted by dizziest at 5:33 PM on July 14, 2011 [1 favorite]

As someone who had a very similar series of fights with her boyfriend-now-husband, I would beg you not to psych her out. I would take something like that like a Carrie-level tease.

Definitely do it early. Possibly as you're backing out of the driveway. That way it will definitely be a surprise!
posted by KathrynT at 5:50 PM on July 14, 2011

I proposed without a ring. She knew it was coming, and the time was right, and I'd left the ring hundreds of miles away anyway, but it didn't matter. Because the timing was right. Carry that sucker around with you, and when you feel it, do it.

Here's my second suggestion: do the fun psych-out gifts afterward. Like "I'm so excited to propose that I'm doing it again! and again! and again!!! I constantly tell my wife that she's lucky we're already married or I'd marry her. and I mean it
posted by TheNewWazoo at 5:51 PM on July 14, 2011

Give her the cute little gifts after the ring. You might really piss her off by setting her up for a ring and then not giving her one. It seems a bit cruel, frankly.

Another suggestion: don't switch hotels in Portland. Just choose one and stick with it. Having to change places every night will get old.

Also: sometimes coastal campgrounds get full on the weekends, especially ones that are an easy drive from Portland, Salem, and Eugene. You might want to make sure they aren't close to getting full now and risk not having a room. Also, a nice surprise might be a nice B&B at the coast rather than camping the first night. The coast can be chilly, so this could be a cozy, romantic treat.
posted by bluedaisy at 9:26 PM on July 14, 2011

If I had your choices I would propose at Crater Lake, which is one of the world's real wonders.

Then, in Portland, I might drive into the Columbia Gorge and go up to Crown Point -- another good place for a sweet gift in a ring-shaped box -- and then to Multnomah Falls and/or the fish hatchery (where they have a free underground tunnel where you can go peep underwater at ancient sturgeon). Or I might go pick blueberries on Sauvie Island.

When you're in Portland and want a nighttime tea/cake/hookah in a magical place, try the Pied Cow coffeeshop, which has a cool night garden.

On the way home, I'd stop at Fern Canyon and drive the Avenue of the Giants.

Congratulations, and have fun :)
posted by hungrytiger at 9:58 PM on July 14, 2011

Lithia Park in Ashland, OR (right off I-5 as you get into OR) is one of the most beautiful parks I've ever seen. And the town of Ashland itself is very romantic.
posted by virginia_clemm at 9:00 AM on July 15, 2011