I feel hopeless in the modern dating world

My Situation and Background I’m a 23-year-old man with little to no experience in dating. During my childhood and teenage years, I was very shy, which kept me from forming relationships or having experiences with girls. Currently, I’m still a virgin, and although I’ve grown both physically and emotionally, I continue to struggle with insecurities.

Personality and Self-Image I’m introverted and often described as a more "feminine" man. I also have a tendency to people-please, which isn’t seen as attractive, not just in dating but also in social circles. I’m aware of this and am working on finding a balance and becoming more confident. Physically, I’ve undergone significant changes in recent years. I work out regularly and strive to maintain a good physique. However, I’ve started losing my hair early and decided last year to shave my head completely. While practical, I’ve noticed that this has added challenges to dating, especially with women my age.

Living Situation and Related Struggles I still live with my parents while I’m studying, which is common but adds a layer of complexity to my dating life. If I were to be intimate with someone, I honestly wouldn’t know where to go or how to handle that situation. This uncertainty is another factor that makes me hesitant to pursue dating actively.

Dating Experiences My insecurities have often held me back from approaching women. Two years ago, I had feelings for a girl who was already in a relationship, so I never acted on them. Recently, I asked someone out on a date for the first time. She was someone I had a good connection with and had already met once. Unfortunately, she rejected me and told me she only saw me as a friend.

Current Struggles and Questions

Confidence: I’m working on improving my self-image and becoming less of a people-pleaser, but it’s a slow process.

Style and Appearance: I struggle with how to improve my clothing and overall presentation.

Living Situation: Living with my parents makes intimacy challenging, and I’m unsure how to navigate this.

Dating Approach: I’m unsure how to approach women and build genuine connections.

My Question I’d appreciate tips and advice on how to boost my confidence, improve my appearance, and find a healthy, respectful approach to connecting with women. How can I grow in these areas while navigating my current living situation and without losing myself to unhealthy beliefs?