I'm a 30-year-old single man.

I’m in my 30s and new here. As Papercraft’s answer suggests, I feel that many women sort men into categories—romantic prospects, friends, papas, and so on—to organize their feelings and decide how to interact with them. So if you make a move out of nowhere, she may say, “That’s not what I had in mind.” It might be better to start by somehow showing that you’d like her to see you as a romantic prospect. Make good use of Christmas and give it your best shot!

I’m だて◎ゆめ, a male member. From the wording of your question, I get the impression that you’ve had a relatively casual relationship. In a sense, she probably thinks you’re a good person even though she knows your situation, which may be why the relationship is still continuing. The issue, as Mac-san said, is how to express your true feelings without being misunderstood as someone just looking for “free sex.” What would I do? I’d probably continue your current relationship style for the time being, then bring it up with something like, “We’ve been seeing each other for quite a while now—would it be okay for me to start thinking about marriage?” After that, please move forward with everyone else’s advice as well. This is one of those moments when you don’t want to regret staying silent. Good luck.

I’m a male member from Seattle. First, you need to calmly assess whether she’s genuinely interested in you. Is the sex merely going through the motions? Has she ever told you that she likes you? If not, it’s absolutely not going to work. If she does seem interested, you shouldn’t stop giving her an allowance until she tells you she no longer wants it. Traveling together is a good idea. Since you’ll be spending a long time together, you’ll get to see each other’s true nature. If you can’t make it work even for a mere three days, there’s no chance of having a relationship.

I’m Paper Airplane, a male member. I know a woman in her late 20s who joined a dating club and is also looking for a marriage partner. She’s involved in papa-katsu (compensated dating in Japan), private dating (dates without an allowance), “fans” (men who simply like her one-sidedly and act as convenient helpers), and marriage hunting. She’s serious about marriage and is really worried about whether she’ll ever be able to get married. Apparently, she meets some very wealthy men through the dating club. On the other hand, when it comes to marriage-oriented dates, she complains that they go Dutch from the very first date, sometimes at a shabby izakaya-style restaurant. Despite enjoying that kind of luxury, she says, “There’s no way I can handle dating an ordinary guy my age.” Yet she’s worried about marriage because she’s thinking about her career and future. It’s amusing—or maybe just puzzling—and I’m amazed by the gap between her innocent attitude and her actions. So, I guess you really can’t understand what’s in a young woman’s heart. Even if she doesn’t seem to want marriage on the surface or through her actions, I’m sure the underlying dream of being a full-time housewife remains a powerful, hard-to-give-up desire for many women. Maybe it’s simply the naïve idea that she wouldn’t have to work… By the way, she says she wants to keep playing around even after getting married.