Letters From Japan: “The Guy I Met Online Wants To Go On A Trip Together. Should I Say Yes?”

Savvy Tokyo's resident "Love in Japan" columnist, Hilary Keyes, answers anonymous questions from readers on everything from dating in Japan to women’s health issues. Got a question you’d like to ask Hilary? Email it to editorial@gplusmedia.com with a subject "Ask Hilary."

Hi Hilary,

I read about your article the other day and I wonder if you can help me with my situation. I’ve met a wonderful funny Japanese guy online and we’ve talked basically almost everyday for more than 5 hours in a day for the past 3 weeks. And he asked me out on a 2 days 1 night trip to an amusement park and close-by attraction sites. He asked me if I want to share a room with him. I politely declined, saying I’d be much more comfortable if we stay in separate rooms. I thought he would ghost me but he didn’t. He keeps talking to me and despite how he points out how it’ll be nice to share a room together one time, it’s still fun talking for hours with him. Should I meet him or shouldn’t I? Thank you in advance. Best regards – A Curious Girl

Dear Curious Girl,

This is an altogether different situation from asking to have a first date at his place and one that, on the surface sounds pretty positive so far. As long as he isn’t trying to pressure you into staying in his hotel room, then I think this sounds like a reasonable idea.

However, if he is trying to pressure you into staying in his hotel room, or says he will book a room for you and tells you the details later — those are two very big red flags that you can’t ignore. If you can’t book your own accommodations for that night (or he doesn’t show you a proof that he had booked separate rooms as per your request before you go), then I think this date should be postponed until sometime in the future for if/when you two are comfortable sharing a room together.

But before all that, it’s better to meet your online beau in person somewhere neutral first, before any park tickets or accommodations are booked. Like, say, meeting up and going to a cafe or restaurant for lunch or dinner at a neutral train station. This is a practical and easy way of seeing if your Japanese guy is as wonderful and funny offline as he is online. Amusement park dates are pretty amazing, but they can also quickly turn sour if things aren’t compatible between the two of you, and it becomes an awkward, uncomfortable situation.

It’s better to meet your online beau in person somewhere neutral first before any park tickets or accommodations are booked.

I once went to a theme park to meet up with a former co-worker turned romantic interest. In the office, he had been a hilarious, charming guy, but on our date, he was a clingy, bratty guy who only wanted to check out his favorite attractions and was pretty pushy about what he thought the date should end with. It did not end the way he wanted, and he disappeared out of my life in a snap. It kind of soured my experience of the park for a while, until I went back and made better memories there with friends.

Don’t get me wrong, I think amusement parks are great date spots — they have plenty of attractions that cater to different interests, which make them wonderful places to see how well both your interests line up. Plus, they tend to be generally very safe as well, so as far as locations go, they’re ideal in that regard.

But they are also typically located outside of major cities, which can cost you a lot in terms of travel (both time and money), park tickets themselves tend to be pricey, and accommodations nearby can be just as bad. While he sounds more than willing to pay for a two days-one night amusement park experience, are you able, and do you want to do the same? Being the holiday season, I know money can be tight for some, especially if you have winter break travel plans, so honestly asking yourself if you can afford to spend those extra yen at the moment is important.

If he isn’t pressuring you, you can book your own accommodation, and you don’t have to worry about your finances for a date like this, then go for it. Have a wonderful time, get to know your guy offline, and I hope for the best for you. If not — maybe put the date course on the backburner for now, and get to know one another somewhere in the city first instead.