Help a boy wow a girl.

January 25, 2007 5:18 AM

My best friend is trying to make a major play to win back the lost love of his life. She left years ago, but has recently started gravitating in his direction. They're getting to know each other again, and the time is approaching when he needs to really make his intentions 100% clear -- he wants to surprise her with an adventurous getaway. However, because of a story that is too long for this forum, this all has to take place in the space of about 36 hours door to door. So, what do you recommend?

This girl doesn't get out of town much due to responsibilities and lack of adventurous companions. However, she's a very adventurous girl herself and so my pal wants to really knock her off her feet with a surprise trip SOMEWHERE where they can have a great time, talk, reconnect, and hopefully fall in wuv. She's very artsy, athletic, loves to surf, quirky, not a big partier (clubbing in NYC or something wouldn't really hit the mark). So where should he take her? Cost is not a very big issue -- he'd be willing to drop $1500 to have this come off smoothly, but she wouldn't be impressed if he was just throwing money at something, either -- creativity is key.
Here are the parameters:
He's going to wait until the time is right to spring this, and has to probably work his mojo for another 2-3 months before he can think about kidnapping her for a getaway, so this probably will take place in April sometime.
Overall, simplicity is best (possibility of direct flights, short travel times, etc) given the time constraints.
1. extra points for a warm beachy location where one can swim or preferably surf. we were thinking something off the coast of carolinas or something, but don't know where to start there. Open to anything, though -- something cultural, really unique, really different.
2. extra points for a good recommendation one a spectacular campgrounds where a small fire can be had. Camping is not 100% requirement, other recommendations are welcome, but this is a girl who LOVED living in a tent on the beach in Hawaii for 6 months, so camping is definitely up her alley.
3. has to be within short flying distance of Coastal NH/ME (within 4 hours flight). Flight can originate from Boston airport, Manchester NH airport or Portland airport, so there's lots of options there. International probably isn't an option because a) too far and b) he wants it to be a surprise and she doesn't have a passport.
4. final destination should be reasonably close to an airport (within 1-2 hrs drive) and rental cars should be easily available at the airport. Overall, the shorter travel time involved the better.

Any suggestions about what he can do to make this really special for her would be appreciated.

posted by Soulbee to travel & transportation (37 comments total)

Are we sure this girl is okay with being kidnapped by her ex?
posted by thirteenkiller at 5:48 AM on January 25, 2007 [1 favorite]

I am a woman (and a lesbian). I had a negative reaction to this romantic "kidnapping." If a woman sprung something like this on me, I'd be offended. Surprise me with a small gift, sure, but spend $1500 on a trip I may not want to make...it feels disrespectful. That's a lot of pressure on her, too.
posted by Carol Anne at 5:49 AM on January 25, 2007 [1 favorite]

All he needs to do is take her out to a cafe, buy her coffee, and sit and tell her he loves her. Forget the kidnapping, because that won't work as well.
posted by wheelieman at 5:55 AM on January 25, 2007 [1 favorite]

Yay, it might put too much pressure on her, all of sudden.

But going on the idea the he knows her better than some anon strangers on the map try this:
http://www.nynaturalwonders.com/explore.php

Though it really might be better to talk it over with the girl and say "Hey let's go somewhere, lets plan a trip"
posted by Brandon Blatcher at 5:58 AM on January 25, 2007

Oh, fer feck's sake. "Kidnapping"? She can SAY NO.

However 36 hours is way too short. It's going to be spent travelling and setting up tents etc.

I'd suggest actually *asking* the chick in question and then organising a week long trip to SoCal, someplace like Carpinteria or Half Moon Bay which has great on-beach campsites, awesome surfing and everything else they seem to enjoy.
posted by unSane at 5:59 AM on January 25, 2007

Thinking more about this more, there's no reason it can't work if the situation is prepped first.

Have him mention to her the idea of just suddenly kidnapping her for some short, adventurous trip. Bring it up several times in a casual manner into she starts to realize he's serious. If she's down with that, then simply have her agree to be suddenly whisked off at some point. Hell, tell her to have a bag packed with the things she'll need and then do it within two to three weeks.

Prepare him to be let down though it sounds like a great idea is she's up for it.
posted by Brandon Blatcher at 6:03 AM on January 25, 2007

Googling Maine adventure or New Hampshire aventure travel or trails brings up lots of results.
posted by Brandon Blatcher at 6:06 AM on January 25, 2007

Instead of kidnapping her, why not arrange a springtime, early morning hot air balloon ride? It can be done right near where they live.
posted by onhazier at 6:22 AM on January 25, 2007 [1 favorite]

Maybe rent a house on North Carolina's Outer Banks? Though it won't be warm enough for swimming until a bit later in the year, it seems to fit the bill.

I had a friend who spent a summer in Rehoboth Beach in Delaware and loved it, though ditto on the not being warm til summer.

Acadia National Park might not be much of a 'getaway,' but I've heard it's beautiful, there is a beach (though not a very warm one) and you can camp and build fires.

Along those lines, there's usually lots of adventure-y things to do in ski towns during the green season: maybe check out Stowe, Sugarbush or Lake Placid.

I wouldn't recommend going too far, because whatever time is spent on the plane is always added to significantly by the time it takes to get to the airport, go through security, and so on. If you only have 36 hours, spending a quarter of them in an airport is probably not going to impress her.

(And this is of course all assuming your friend is certain his ex would like something like this, is prepared for the possibility that she might find a vacation together to be too much all at once, etc. etc.)
posted by AV at 6:34 AM on January 25, 2007

How about skydiving?
posted by infinityjinx at 6:36 AM on January 25, 2007

Guys, I'm sure "kidnapping" was just a friendly euphemism and that this man is not really going to kick in her door, tie her up and force her on a vacation. All of these "I DONT THINK THATS A GOOD IDEA" answers are very much not in the spirit of AskMeFi, which is not called "Ask What MeFi Thinks" for a reason.

That said, there are plenty of hike-y, camping adventures available in New England and if it's warm enough by then, there are trails that lead out to beaches and whatnot.

If you want to head south, Cumberland Island is off the coast of Georgia. Beach camping, backpacking and wild horses! Average temp. for winter is around 60, which is comfortable.
posted by GilloD at 6:40 AM on January 25, 2007

Little St. Simons Island off the coast of Georgia. It is rustic. It is a private nature preserve with hiking, biking, boating, good meals and lots of nature. Wide range of activities. There did not appear to be good surfing waves on the beach when I was there.

This is a really neat place. A lot of privacy and possible group interaction if wanted.
posted by JohnnyGunn at 7:02 AM on January 25, 2007

Montreal?
posted by LarryC at 7:18 AM on January 25, 2007

My first thought: is this girl me? Then I realized I haven't camped in Hawaii for six months. Oh, well.

Oh, fer feck's sake. "Kidnapping"? She can SAY NO.

It's not the idea of 'kidnapping' that's sending up 'Bad Plan' flags for me. Of course she doesn't have to go. The question is whether he's giving her enough information about his feelings to allow her to make the right decision.

If he's not clear about his intentions on the trip, it could be the most miserable 36 hours of their lives. Let's say she's not on the same page as he is, just happy to have a friendship developing with a former lover. So imagine this: he says 'let's have an adventurous weekend getaway,'and she says 'great! How nice that I have this amicable relationship with my ex and we can even travel together and have fun as friends and maybe talk about our latest crushes and stuff.'

Fast-forward to the first night by the campfire, stars out, bourbon-and-coffee, crickets singing, whatever -- and he springs the big romantic spiel on her.

And she's not interested.

And now she realizes the whole thing was a Grand Plan to get them back together, and now she's stuck there with him until the end of the trip, and they have to have a long miserable heart-to-heart where she straightens him out on her feelings or lack thereof, and they have to spend the remainder of the 36 hours together going through the awkward motions of the planned activities that are now robbed of any joy.

Is he prepared to take this risk? Is it a fair thing to do to someone?

BUT, in the spirit of AskMe, I will set aside these questions for the moment and assume that all indications are that she wants him back.

I suggest flying into Baltimore, renting a car, and heading out for a camping trip to Assateague Island. You can camp on the beach. There's surfing and swimming (though it may be cold in April; still, a surfer can bring a wetsuit and tough it out). There's hiking and biking and kayaking. Nearby is the island of Chincoteague, famous for the wild pony penning (and dear to many of our inner 3rd-graders because of Misty).
posted by Miko at 7:20 AM on January 25, 2007

Some more thoughts. Relationships arn't about winning someone over. It's more about relating to someone. We seem to forget that it's not about you getting what you want, its about each other. Don't try and wow her yet. Just sit down and see where each other is at as far as feelings. Don't overdo it.
posted by wheelieman at 7:30 AM on January 25, 2007

How about driving down the Cape and renting a cozy winterized cabin there? Make sure it has a fireplace. And for the girl's sake, make sure it has two bedrooms or at least two beds in case she doesn't just want to jump into the sack with this boy. Also, the proximity to your friend's home location would be pretty nice if this girl tells him to eff off. The Cape on the off season is quite nice, relaxing, and somewhat romantic.
posted by nursegracer at 7:35 AM on January 25, 2007

nursegracer reminded me that Martha's Vineyard is particularly nice in April, and has the same advantages of the Cape while still feeling like you've gotten far away. Great beaches and walking trails, plus restuarants and bars with music, so you can have the best of both indoor and outdoor activities, civilzation and nature, and many options for things to do if it does get awkward.
posted by Miko at 7:45 AM on January 25, 2007

The surprise does not sound like a good idea to me. I think wheelieman said it well: "Relationships aren't about winning someone over. It's more about relating to someone. We seem to forget that it's not about you getting what you want, its about each other. Don't try and wow her yet. Just sit down and see where each other is at as far as feelings. Don't overdo it."
posted by caddis at 8:11 AM on January 25, 2007

Springing an expensive trip on somebody without their ability to plan on it is a terrible idea. Particularly in the situation where you describe. I don't know the circumstances of why they broke up, and it's a sweet gesture, but making presumptious plans, booking plan tickets, and assuming that you can take over somebody's (assumedly precious) free 36 hours in order to woo them sounds like a recipe for disaster. I would be furious, because I would feel like I had to go - it's a grand gesture and expensive and I would feel like a total jerk turning them down - and then I'd never, ever enter into a relationship with said person.

If money is no object, why not organize a planned day of surprises? The Hot Air Balloon ride sounds very cute and right up the correct alley.

"Hey love of my life, will you spend Saturday with me? I want to take you someplace fun. It'll be a surprise. You'll be home by midnight."
posted by pazazygeek at 8:20 AM on January 25, 2007 [1 favorite]

I dont have activity suggestions but I'd like to ditto Brandon's suggestion to at least give the girl a head's up even in jest. One of my past boyfriends sprang a last minute trip to San Francisco complete with cirque du soleil(sp?) tickets. It was a great trip and a 3 year relationship came out of it. But it's been five years since we broke up and I still feel a shadow of irkness when I think of the presumptuous nature of his well intentioned actions.
posted by like_neon at 8:27 AM on January 25, 2007

I agree a get away too much.
Sleeping arrangements could make things VERY weird and possibly a big turn off.
posted by beccaj at 8:28 AM on January 25, 2007

This sounds like a VERY bad idea. Not only for the reasons mentioned throughout but because a there-and-back trip in 36 hours sounds stressful and will probably invite crankiness, travel weariness, etc. These things are not conducive to the end goal.

Why don't you suggest that he plan a local day trip. A hike, scenic drive + picnic or something like that. She is going to remember why she once fell in love with him if she remembers how much fun they had together. Hours on a plane, in an airport, etc. is not fun.
posted by necessitas at 8:48 AM on January 25, 2007

Come to Utah and go snowboarding. 11 resorts within an hour of the airport and the greatest snow on earth, well not so great this year, but, you'll get the idea.
posted by trbrts at 8:54 AM on January 25, 2007

We have no idea what these two are really like or if this will be a good idea or a total cluster fuck. Hell, this isn't even for the guy who posted it; it is for his "best friend". He didn't ask if it was a good idea or bad one, just where he should go. Why all the negative waves? He is not asking for advice on whether or not to do it.
posted by JohnnyGunn at 9:10 AM on January 25, 2007

Why all the negative waves? He is not asking for advice on whether or not to do it

I think most of the people who responded want to see his friend get the girl. It is hard to offer good suggestions for where such a bad idea should take place.
posted by necessitas at 9:17 AM on January 25, 2007

I have to side with necessitas: if this pal has you polling the internet for ideas, he should probably know that 90 percent of the people responding thinks it is a bad idea. Because it is a bad idea. If she is on the fence at all about him this transparent power play for her affections will put her terribly on the spot: it could even force her away from him by making her feel like she is being pushed to go too far, too soon. It is, frankly, manipulative. I'm sure your friend doesn't see it or mean it that way but it is.

It is also dumb and wasteful. This is a gimmick. Well, call me the king of cliches but solid relationships are not founded on gimmicks, they are founded on honesty. If friend is simply honest with this woman he might be kissin' her up this weekend, rather than waiting 2 to 3 months hoping Supervacation will somehow make it easier for him to say what he actually feels, or maybe just eliminate the need for uncomfortable, vulnerable honesty altogether as they are swept away on a tide of cinematic romance.

So, 1, tell your friend to just come out and tell her already. Chances are she already knows his interest is renewed - and she already knows which way she is tending. 2, tell your friend to buy himself a $5 Metafilter account. And 3, next week or so, your friend can ask his first question, either, help me plan a surprise vacation for the love of my life whom I've recently started dating again or help me get over the love of my life not wanting to date me again after all.
posted by nanojath at 9:49 AM on January 25, 2007

1. Bad idea &c.

2. I just flew from Portland to Puerto Rico for a week in Rincón, a laid-back surfer's paradise - in fact the ISA World Masters are happening right down the hill from me this week. JetBlue connects through JFK so it's a bit longer than 4 hours travel time. Aguadilla airport has rental cars and is about 30 min from here.
posted by nicwolff at 10:47 AM on January 25, 2007

I lived in Puerto Rico for about a year, and I too was going to suggest Rincon. It's a tiny little town, not too touristy, and it's pretty mainlander friendly because of the surfing background. Also, there is "hostel like" accommodations that are really reasonable. There is also a cool bar/restaurant/surf shop (at least there was 10 years ago). Flights are usually pretty reasonable from the east coast (you would fly into San Jose, and Rincon is probably a 90 minute drive). Puerto Rico is part of the US, so no passport, currency, visa, language hassles.
posted by ill3 at 11:15 AM on January 25, 2007

I got really excited by this question because its something I've always wanted to do with a girl I was in love with. At first when I read all the 'bad idea' posts, I was like 'hey those guys are jerks. This is a great idea!'. Then the word 'presumptious' was said and I realized they actually had a point. I hate to admit it, but they actually had a point. That sucks! At least I read this before I ever fedex'd a surprise plane ticket to a girl (... yep. i truly wanted to

So here's my answer:
First, don't do it unless you guys are at least kissing again. If she's not kissing you, then 99 times out of 100 she doesnt want to. This 'magical reunited and it feels so good' kiss should happen way before the trip.

I think the best way to do it is for him to say 'sweetheart, I want you and I to get away for a day and do something amazing. Would you be interested in something like that?'. Be prepared to tell her your ideas and also make sure she knows you are very open minded and just want to spend time with her building unforgettable memories.

I'd vote driving to a nearby lake/beach/mountain and camping. Flying will eat too much time out of 36 hours (probably) and 36 hours isn't enough time to both be amazed by how cool the adventure is and at the same time amazed at how great the new relationship is.

I'd vote Puerto Rico if you could score more time for the trip, for around $250-300 round trip you could leave on a friday and get back on sunday and still have an awesome time. I loved my trip there with my new sweetie

and good luck!
posted by ZackTM at 11:18 AM on January 25, 2007

ill3: Actually JetBlue flies right to Aguadilla for about $200 round trip. And yes the bar/cafe/surf shop at Maria's Beach is still there - I had a steak burrito there for lunch.
posted by nicwolff at 1:25 PM on January 25, 2007

All I can think is Lame 3.0.

Go out for a hot chocolate on a cold night instead.
posted by dropkick at 2:11 PM on January 25, 2007

I'm going to disagree with all those calling this a bad idea. Yes, it is presumptious, and it stands a decent chance of not working out well if she does not return his feelings. But after this experience he will either have gotten a relationship going, or it will be very clear that it's not going to happen and both can get on with their lives.

Just don't try to fly somewhere and go camping in a 36 hour time period. There's to much air travel and camp setup in that to leave much time for adventure, and if she lived on a beach for 6 months, setting up and taking down camp probably was not why she liked it.
posted by yohko at 3:18 PM on January 25, 2007

I think the balloon ride/day trip/local outing is FAR superior.

But, I also think all these people screaming kidnapping and going on about presumptuousness are wired very different than other people. I can't quite understand like_neon above... she did it, enjoyed it, it was successful, spawned a 3 year relationship, yet she STILL is bothered by it? I simply don't get it. *shrug*

But, this shows that it is CRUCIAL he find out which way she is wired *BEFORE* he concocts such a scheme.
posted by Ynoxas at 3:22 PM on January 25, 2007

I'll second San Juan. With a little extra time you could take a boat to the island of Culebra. Wow is that a nice trip with world class beaches, very romantic. I went there with my girlfriend.

However, I need to agree with everyone else that's saying this is a bad idea. It's too much to spring on someone, and could easily leave her feeling overwhelmed. A $1500.00 gift is certainly more than I would feel comfortable accepting from someone, and I might resent the pressure.

Instead, I would recommend the "cool date" idea. A romantic dinner, theatre, this balloon thing, whatever SHE likes. Then kiss at the end of the night and say something romantic. It's okay to bring up wanting to take her away somewhere where they can get to know each other again at that point too.
posted by xammerboy at 3:32 PM on January 25, 2007

save your money and find a girl that really likes you - it shouldn't take a bit getaway
posted by Salvatorparadise at 7:14 PM on January 25, 2007

thanks for all the suggestions and for the people who understood that he doesn't mean kidnapping in a literal sense. there are many good points here. He is going to wait until the time is right between them; she will know his intentions before going. he has planned to obtain 2 hotel rooms or 2 tents for the occasion. vineyard/nantucket sounds great. Thanks for the suggestions!!
posted by Soulbee at 5:19 AM on January 26, 2007

vineyard/nantucket sounds great.

Just a heads-up -- Nantucket is 'quieter' (i.e., crik crik, crik crik) than the Vineyard, especially at that time of year. So if it's going to be a very quiet, walk-on-the-beach and read-and-chat-quietly-all-day vacation, that would be a good choice. However, if they're active and want things to do and to be social, they should aim for the Vineyard. There are just as many beaches and quiet spots, but there are also bookstores, cafes, restaurants, and places to hear music. Just a note about the relative character of each (they're quite different).

There are a couple old Ask.Me threads on the Vineyard and Nantucket - be sure to check those out for recommendations.
posted by Miko at 7:34 AM on January 26, 2007