I’m prepared for criticism, but could I ask for advice about love?\n \n I’m genuinely struggling.\n \n I’m a 24-year-old woman, and I don’t know how romantic relationships work.\n\nI’ve never had a romantic relationship with a man. More precisely, I had my first experience at 17 with a man in his 50s whom I met through a dating site, for 500,000 yen.\r\nSince then, I’ve spent seven years doing papa-katsu (compensated dating in Japan) and being someone’s mistress, and I’ve never once dated a single man I could actually call my boyfriend.\n \nI’ve come to see men in terms of profit and loss, so I don’t understand what it means to genuinely like someone.\n \nEven so, there’s a man I’ve been in a strange, dinner-friend-type relationship with for about two years.\n \nHe’s 15 years older than me, divorced, and we met through university-related activities. He has nothing to do with this kind of world.\n\nTwo years ago, he pursued me intensely, but at the time I saw “older men” as “people who give me money,” so I decided to cut my losses when I realized there would be no financial benefit to the relationship. I stopped contacting him for nearly a year and nine months.\n \nAround February this year, I suddenly decided to reach out to him. He replied right away, and we’ve gone out for dinner about seven times since then.\n\nBut nothing has progressed, and we’re still just having dinner together (crying).\n\nWe meet at 6 p.m., eat until 8, he takes me home by taxi, and then we part ways. That’s all we ever do.\n\nI think we both know that we have mutual feelings and could start dating if things continue this way.\n\nHe also says and does things that suggest he’s interested, but since he hasn’t confessed his feelings or made any direct moves when we meet, we’ve ended up remaining a dinner-only relationship.\n\nSome of the things he’s said include:\n\n・“You seem different! You’ve become even more beautiful!”\n・“I don’t think any man would turn down ○-chan if she asked him to date her.”\n・When I told him over LINE that I liked him, he replied, “I like you too.”\n・“The age gap is so big that I feel guilty, as if I were dating my daughter.”\n・“If I get the chance, I’d like to remarry.”\n\nThose are the kinds of things he says.\n\nOn the taxi ride home, we always hold hands and chat.\n\nEven though we’ve known each other for nearly two years, we still haven’t even kissed.\n\nRecently, before we part, he’s started saying, “I’d like to spend more time together next time.”\nSo I reply, “Yes, I’d like to take our time together too.”\n\nI interpret “spending more time together” as staying overnight, but instead of taking things slowly, we always finish after a two-hour dinner. He also eats incredibly quickly, so the whole thing feels rather rushed.\n \nI suspect he’s more timid than I expected and doesn’t have the courage to confess his feelings himself.\n\nThat said, I don’t believe he’s only looking for something casual or treating me carelessly or looking down on me.\n\nDo I have no choice but to encourage him to confess and suggest staying over myself?\n\nIf so, how should I invite him?\n\nUntil now, my only experiences have been adult relationships (intimate) with married men for physical purposes, relationships through dating clubs, and working as a hostess. I don’t know how real romance is supposed to progress.\n\nUsually, I just went along with the flow: having conversations centered around the man that weren’t particularly interesting (sorry), then going to a hotel. But ordinary romantic relationships have all sorts of steps and proper timing, and I find it difficult.\n\nAlso, compared with how much I’ve earned so far, I have very little savings, and I haven’t been able to stick with a job for long. It’s my own fault, but I feel hopeless about my life.\n\nPart of me can’t take the next step because I feel guilty, wondering whether someone like me is even allowed to have a normal romantic relationship with a decent man.\n\nWhat do you think this man is thinking, and how should I move this relationship forward?\n\nOr should I be more bold and approach him the way I would a married client from a dating club or a customer from my hostess work?\n\nI’m sorry for the long post.\n\nTo those with more experience in life, could you please give me some advice?\n\nI’m asking this prepared for harsh or blunt opinions as well.