I flew across the country to see her

Sorry the site was down yesterday. Please give yesterday's letter some advice love – it wasn't seen for much of the day.

Also, there's a new bonus episode of the podcast that happens to feature someone talking about how they met a romantic partner in the comments section of this column.

It's Thursday, so we chat at 1 p.m.

I've listened to the Love Letters podcast and was hoping to get some advice. I met this woman last year at work. We were at a training convention, and on one of the free nights we ended up hanging out with mutual friends. We immediately started talking and it was great. The group as a whole hung out all night, but she and I spent a lot of time talking to each other. A day later, we all returned to our separate offices and didn't talk for six weeks.

Fast forward, and everyone at the company went to Disney World. We met up there and hung out for most of the four days of the trip. We went to Magic Kingdom with my friends, and went to an arcade the last night, just us two. We had breakfast together right before our flights and parted ways. Nothing happened, no kiss, nothing. I think I had some chances but I never took them.

Then, six months later, I told her I had to go to her city for a convention, when in reality it was to see her. I flew from my city and we had dinner. We had great conversation and a great time together. We walked around downtown and parted ways again for the night. My friends had told me to make a grand gesture and I wanted to, but then I decided not to in the moment. I thought that even if I tell her how I feel, nothing can happen because I'm in my city and she's in hers (halfway across the country). I figured, let me at least keep the door open and see what happens in the future. So I flew home a few hours later and that was it. We still text once a month and it's not dry at all, but I'm just wondering what you think.

Did I waste an opportunity? I still care about her, and if we lived a lot closer I would've already made a move, but the distance and the fact that both of us don't really want to leave our cities keeps me from letting my feelings out. I was curious to know your thoughts.

– Thinking About Her

I don't think you missed an opportunity. Also, I'm not big on grand gestures, at least not at the start of a relationship. Dramatic speeches raise the stakes so much – often too much if they're made before there's even been a real date. You followed your instincts and enjoyed her company. There's nothing wrong with that.

Also, you learned that spending more time with her only made you want to, well, spend more time with her. That reminds me of all the people in Season 2 of the podcast who had a revelatory moment about a maybe-significant other because they realized they missed them. It was a recurring narrative, that a person had a few great dates with someone, went on vacation, and then realized, "Oh, all I want to do is return to them."

In your case, you might be realizing that you're more open to long-distance than you were six months ago. I mean, maybe not. Maybe that boundary is still important to you. But ... you flew across the country to see this woman. And if you're going to think about her all the time, analyzing texts and wondering when you'll have quality time with her again, you might be better off spending that energy on making it happen.

You'll have to go with your gut on that. It's possible that distance/moving is off the table forever, and if so, try to focus on others. But if the trip to her city felt necessary, you should think about what that means.

– Meredith

Readers? How do you know if you should be open to a long-distance relationship? Does your company take you to Disney World?