Jump to content

Is this too over the top for a second date?


LiteWait

Recommended Posts

Had a nice first date with someone a couple hours away, she actually had vacation abroad planned for the next few weeks, so planning a second date. Exchanged a few messages since the first date, my read is things are going well. We are both _very_ active 50+'s, dinner and show (or something like that) for the second date I think would be boring for both of us, we both love the outdoors. This may be a third or tenth date...but I want to propose this as our second date, namely I'd rather both of us have fun no matter how the relationship goes:

 

1. Pick her up mid-afternoon and drive about 3 hours to a Inn and have dinner

2. I'll book separate rooms for us, after one date certainly anything else would be a bad idea!

3. Next day snowmobile up in the mountains

4. Return her home that night

 

I'll foot the bill, no way I'd propose something like this and expect her to pay.

 

Reasoning and worries:

 

o Reasoning: I want to have fun, can't really think of anything during the winter knowing our personalities to do local.

o Worries: On the flip side, I don't want to scare her by this being too radical a second date, or make her uncomfortable heading out of town for a night with a guy she just

barely met. Also, even though I could care less about the money, she can do the math probably $800 or so which again make her uncomfortable.

 

Question 1: Is this too over the top?

Question 2: If it isn't too over the top, how should I propose this so as to make her feel the most comfortable?

 

Advice appreciated.

Link to comment

Wait a while for any overnight thing. Even if you emphasize separate rooms, there is to much room for misunderstandings. It's also a bit too much too soon.

1. Pick her up mid-afternoon and drive about 3 hours to a Inn and have dinner

2. I'll book separate rooms for us, after one date certainly anything else would be a bad idea!

Link to comment

Wayyy OTT for a second date, but also a bit freaky for someone who doesn't know you yet. Not just the overnight stay, but the three hour drive to an unknown location; that would unnerve me with someone I didn't know.

 

Your idea is more the kind of activity which would be great if you had decided mutually if you were in a relationship, but why don't you just stick to dinner and chat while you still get to know each other, without the distraction of other stuff?

Link to comment

Agree with others.

 

Also you mentioned your goal for this date is to have "fun."

 

When you're into each other, you will have fun no matter what you do, heck getting ice cream and walking about town is fun -- again when you're really into each other.

 

You don't need to try so hard to impress her, with money, your sense of adventure or anything else.

 

That, in and of itself, can be a turn off.

 

On these very realy dates, best to keep it low key, relax and get to know each other.

 

Save these elaborate dates for later on, when you're in a relationship.

Link to comment

On one of our very early dates, my bf and I rented bikes and drove to Julien (small country village 30 miles away), explored the village, ate home made hot apple pie, walked about the village, talking, laughing, kissing, clicking, then went to a quant little cafe for dinner, drove home.

 

It was local and relatively low key, but still super fun, adventurous, romantic, intimate.

 

Why? Because we were super into each other!!

Link to comment
Ok, thanks for the input, consider my hand slapped. Really want to find something active we kind of even joked about how lame going to dinner and show or something was.

 

Indoor tennis, indoor rock climbing. I mean there are active things to do in town if you really want to even in winter. However, it seems like you are trying way too hard to impress her and that the negative/critical talk on your first date has left you somewhat on edge about what to do with her. Chill out, she is only human and likely there was more talk and you both showing off than any real comfort developed to actually pursue outdoor activities right now.

Link to comment

The fact that you are even questioning and unsure how to propose it to her it tells me you know the answer to your own question here.

 

If you don't want to do dinner and a show that's all well and good but I am sure there is some middle ground in there... like bundling up and going for a walk, snow shoeing if you have snow, skiing / snowboarding if you have mountains nearby, etc. I am active and love the outdoors but would definitely not be okay with going out into the middle of nowhere with a guy I barely knew, or with the pressure of staying overnight in a hotel with him even if there were separate rooms.

Link to comment

Yup way too over the top. Mainly because it violates her boundaries. that would set a red flag for me.

1) Do not trap someone you are just getting to know on a 3 hour car ride.

2) You have no regard for what her plans are the next day.

3) its too expensive for the stage in dating and if you did propose a trip like this later down the road, you should be collaborating and planning it together.

 

 

if you and she are both outdoorsy, i am sure there is a place within 40 minutes of you that has ice skating, or a winter festival.

Link to comment
For me, an overnight of any type is far too much for a second date.

 

While it's not a bad idea, in terms of the planned activities, I would not be comfortable going away for a weekend with a man I barely know. Tuck away the plan, and save it until you've dated a while longer.

 

 

 

Same. I wouldn't feel comfortable for a overnight date with a stranger on second date even if on separate rooms. It's too much too soon.

Link to comment

That is a whole lot of extra. Being frank, she would or at least should be put off buy a guy who'd feel so compelled to drop 800 bones and drive her 6-hours round trip just to have the benefit of her company. You're establishing very early on that this is the value you bring. And unless the whole sugar-daddy thing is something you two both talked about and want, you should be put off by a woman who would be comfortable taking you up on such a second date. And while I actually agree that a movie on a second or first date isn't the best idea (moreso for the fact two people generally aren't going to be comfortable enough to even be holding hands during it than its lack of novelty), there's a pretty big ass DMZ between that and a weekend in Aspen.

 

Plus, there seems to be some pretty big disconnects going on in your head trying to plan this out. Firstly, that after all your funding, hours of driving her, and her being out of town with a near stranger, you think whether she has a second room could make or break her comfort level. Honestly, I think she'd be more put off trying to figure out why a dude pulling all this isn't even looking for the benefit of a decent lay. And second, how many people in your life who you actually know and like do you think you'd be comfortable spending 36+ hours with? Why make that bet involving someone you've on a single occasion had a decent dinner conversation with?

 

I'll give you the benefit of "based on your personalities, not knowing what you could do in town" just being an excuse to wow her, in which case the others here have offered you plenty of great activity-based ideas, but if the intersection of your interests is genuinely so limited you've got to involve road trips and spending nearly a grand by date #2, it's probably best to stick a fork in this one sooner than later.

 

Others (and I guess myself as well at this point) have drilled it pretty hard that a woman would be put off for any number of reasons, so I'll take this final moment to emphasize that you need to dig up some self-respect and a sense of value into what you bring. You've got a personality as well. You don't need to go over the top with your time and money supplementing it to make it worth her gracing you with her presence.

Link to comment

Wow I am taking a beating, maybe deservedly so. What makes me chuckle is I really have no idea where the relationship might go of course, not even trying to impress her, just wanted something super-fun.

 

That being said, obviously not knowing me, her view of it could (like you said) head in many different directions, none of them good.

 

We can stand down, I learned my lesson :-)

Link to comment

Date at a normal pace. That means, for a 2nd date, I wouldn't go past 6 hours together. If there's a cute town halfway between your homes, where there are quaint shops and bistros, go there for an afternoon of lunch and looking inside boutiques or a local museum.

 

If the two of you worked out longterm, what would be the implications of one of you having to move to close the distance? Is this doable as far as careers and family ties? It's not too far, but could still make a major impact for some in this situation. Make sure you don't waste your time dating her if one of you can't eventually move. Not that you should ask this question on the second date. Just something for you to start thinking about.

Link to comment

Great questions. Already discussed deal-breakers like distance we are both mobile and not tied to any area. 6 hours makes sense as I get my head around this. For us this might be a 6 hour hike as shopping and bistros fall to the bottom of our activity list.

Link to comment

I don't want to pile it on, but: yes, over the top. I remember your earlier post, so I know you're in a bit of an eager state—just recognize that, so you can keep it in check. Because I don't think this whole scenario is even really about her, or impressing her, so much as a reflection of how much you long to be in a relationship. Because, minus the separate rooms, that's the sort of getaway you do with a girlfriend, not someone you're just exploring.

 

It's the sort of thing you might talk about during a second date—like, wouldn't it be fun to ride some snowmobiles some time?—but what are you actually doing while having that talk? Eating ice cream, sipping wine, making eyes, maybe some making out.

 

Reminds me a bit of my best friend. Bless him, love him, but dude is kind of immune to taking things at a normal pace. He spent his whole 20s and early 30s with one person, so he's kind of a fish out of water at 35. Always goes from Bumble date one to something like year 2 with this second date—in his case it's often cooking at his apartment, because he loves domesticity, craves what he had with someone for so long. Still, it always amps things up too quickly—yeah, it's fun to feel like you have a girlfriend or boyfriend, but you have to allow real time for that to develop.

 

I'm no expert, but I do date a lot, and connect well with people. Early dates to me are generally confined to pretty pedestrian stuff: a glass of wine, a meal, a walk around a lake, a beer on a bench. They're about talking and listening. Because, hey, with the right person is there anything more fun that that? Is there anything hotter? Whether you're looking to get laid or get loved, it's not going to come from a baller snowmobile trip at minute five of connection time. It's going to come because someone felt seen and heard and liked what they were hearing and seeing.

Link to comment

Old family friend would rent a plane, and fly his date out for lobster in Maine. He always then complains how they turn into gold diggers. No need to lead with your wallet. You are ENOUGH to enjoy dinner and a show. Focus on getting to know eachother. A dinner and a show is plenty awesome! If you don't want to do a show, and want to talk, go to an art exhibit, museum, etc. But a play, opera, musical is plenty exciting to bond over when you see it together.

Link to comment

Like with everyone else, way too much too soon, and really, how are you normally? Do you travel and spend money like this all the time, or is this something you do on occasion, and you'd rather stay local, maybe even enjoy just being home with a movie, and enjoy these extravagances with less frequency? Lead with future precedence, is what I'm trying to say. Like with texting, which is a serious source of contention with folks. If you're overall not a major texter, don't leap into a relationship and text with a frenzy and then drop off to your normal, nearly non-existent levels 2-3 weeks later...issues abound...so stick to a normal routine, though you may ramp it up a little at first or in a compromise.

 

The thing is, the two rooms and hotel doesn't bother me that much, except for the exorbitant amount of money you would be spending, plus food, rentals...that would be a lot to accept. What would bother me more is being alone with a near stranger (even though I like you) for a long drive, and then being alone in the woods on snowmobiles or whatever. I'm not highly worried about murderers and the like, but it's a bit squicky, and just "off."

 

We all know what hotels and hotel rooms imply, even though you plan on separate rooms...let's be realistic. But despite this, I am wondering if you have some good local resorts for a "staycation," so she can have her own transportation, there are local, public fares, and it's just a little less daunting. I wouldn't even plan this for a 2nd or 3rd date, but maybe a few weeks or months down the line or when you're ready for some intimacy, maybe the timing would be right after a 3rd date, who knows, but seriously, don't lead with this. At 50+, we're not exactly worried about our virginity and iron underwear, but we do need to be picky.

 

As many have said, if you're really enjoying each other, you don't need to have all the thrill of all these external sources. Being together in this new relationship has a habit of being hot and exciting all on its own.

 

Since we don't get snow and it's pushing highs of 67, I really can't relate to the snowbound, claustrophobic nature of weather, but I'm also one that is perfectly happy snuggled at home with a movie or maybe play some pool (I can't play) or bowl (not great at that either), or just grab some dinner, a movie, explore some local light shows, a supermoon event coming up, and walk and talk and freeze. Getting to know each other is the thrill, and you can discuss future date ideas and lengthy (or short) trips and getaways at that time. Surely you have some local options that may not be snowmobiling, but fun just the same.

Link to comment

I think your plan is best left til about date #10 or more. As a woman I would not go on a 3 hr car ride with some dude I barely know. I would not stay over in a hotel even in my own room, with said dude. Too much too soon.

 

Take her to a local event, a hockey game, or whatever sport is near by that she may like. I say that because you mention snowmobiling so you must be in an area with snow. Go to whatever community event is near you. Go to a nearby town and have lunch, see the sites. Go to the movies. Dont rush it!

Link to comment

This sends a message that you are starving and have nobody else in your life with whom you can do this kind of thing.

 

Recognize that if you spend your load shooting out of the stratosphere on date #2, you're setting yourself up to feel boring and inadequate on date #3.

 

Skip that, and relax into getting know one another without showing off.

 

Head high, and enjOy simple pleasures.

Link to comment

Maybe not. She may love it. What would concern me, is setting a precedent. She might come to expect this. If you casually blow off 800 smackaroos, you are signalling money is no option. It might not be to you, but people get real strange around money.

 

I think people are being a bit harsh and judgey wudgey. You thought big, and out of the box. You were smart enough to test the idea here in a safe way. That shows both creative thinking and conscientiousness. That's a good combination.

Link to comment

Archived

This topic is now archived and is closed to further replies.

×
×
  • Create New...