Please let me ask for serious advice, even if I’m going to be criticized.

I’m genuinely struggling. I’m sorry for asking questions repeatedly. I’m a woman in my 20s with Dating Type C. I don’t know how to date. I have no experience being in love with a man. I had my first experience at 17 with a man in his 50s whom I met through a dating site, for several hundred thousand yen. Since then, I’ve devoted myself to papa-katsu (compensated dating in Japan) for seven years, continuing a mistress-like lifestyle, and I’ve never once dated anyone I could call my boyfriend. I tend to view men in terms of profit and loss, so I don’t understand what it means to like someone. Even so, there is a man with whom I’ve maintained a strange, dinner-friend-like relationship for about two years. He is 15 years older than me and divorced. We met through university-related connections, and he has nothing to do with this kind of world. Two years ago, he pursued me very enthusiastically, but at the time I saw “older men” as people who gave me money. Since there was no money involved, I decided the relationship wasn’t worth continuing and cut him off for nearly a year and nine months. Around February this year, I suddenly decided to contact him. He replied right away, and we’ve gone out for dinner about seven times since then. However, nothing has progressed, and we’ve simply continued having dinner together (crying). We meet at 6 p.m., eat until 8, then he sends me home by taxi and we part ways. That’s all we ever do. I think we both know that we like each other and could start dating if things continue this way. He also says and does things that seem like signs he’s interested, but since he hasn’t confessed his feelings or made any direct move when we meet, we’ve ended up as nothing more than dinner companions. The things he’s said that seem to show interest include: ・“You seem different! You’ve become even more beautiful!” ・“I don’t think there’s any man who could turn you down if you asked him to date you.” ・When I told him I liked him over LINE, he replied, “I like you too.” ・“The age gap is so big that I feel guilty, like I’d be dating my daughter.” ・“If I had the opportunity, I’d like to get married again.” Also, we always hold hands and chat in the taxi ride home. Even though we’ve known each other for nearly two years, we still haven’t even kissed. Recently, before we part, he has started saying, “I’d like to spend more time with you next time.” I reply, “Yes, me too.” I take “spend more time together” to mean staying overnight, but we always end after just two hours of dinner. He also eats incredibly quickly, so everything feels rather rushed. I suspect he’s actually quite shy and is the kind of man who doesn’t have the courage to confess his feelings first. That said, I don’t believe he’s only after something casual or treating me carelessly or looking down on me. Am I going to have to encourage him to confess his feelings and suggest staying overnight myself? If so, how should I invite him? Until now, my only experience has been physical relationships with married men, dating clubs, and working as a hostess, so I don’t know how real relationships are supposed to progress. Usually, I just had to go along with the flow—making conversation focused on the man, even if it wasn’t particularly interesting (sorry), and then going to a hotel. But ordinary romance has all kinds of steps and feels difficult. Also, compared with how much I’ve earned so far, I have very little savings, and I haven’t been able to stick with any job for long. I know it’s my own fault, but I feel hopeless about my life. Part of me can’t take the first step because I feel guilty, wondering whether someone like me is even allowed to have a normal relationship with a decent man. What on earth is this man thinking? And how should I move this relationship forward? Or should I be more direct, as if I were dealing with a man from a dating club? I’m sorry for the very long post. I have hundreds of friends on LINE, but they’re all older men. The only family member whose LINE contact I have is my mother. I don’t have a single friend. So, to all of you with more life experience, could you please give me some advice? I’m asking this knowing I may be criticized, so please don’t delete my post...