I (24/M) have always struggled with feelings of loneliness and depression stemming from social anxiety for as long as I can remember.

I think this comes from my own introversion, underdeveloped social skills and a general lack of affection growing up. Now, I don’t want this to be a self-pity post where I complain about how lonely I am because I know this is a long journey to becoming the person I want to be. I’ve made a lot of changes to my life in the past year or so and taken many steps to ‘put myself out there’ into situations where I’m forced to be more actively social; I can confidently say now for the first time in my life, I’m happier than I’ve ever been and I have a few groups of friends and people I can rely on. Even the act of writing this post is something I wouldn’t have done a short while ago so I can at least say that I’m proud of myself for getting to this point.

I never really had trouble in other parts of my life; in terms of career, financial situation, family, it’s all fine for me. But I went to a single-sex highschool and had major anxiety all the time; I’ve managed to make it through my entire life up to this point without ever having a romantic relationship with a girl and I think my lack of romantic success is still a major source of feelings of inadequacy in my life (as if there’s something wrong with me because nobody ever sees me in that way).

I just feel so helpless when I’m with a group of friends and they can so casually talk about sex and previous relationships and all I can do is nod and smile.

What should I do?

I’ve been trying dating recently but don’t get past the first date if that. And I get it for the most part, girls prefer someone charismatic and high energy, which I’m not. I think I can benefit from learning to be a bit more like this but I also don’t want to feel like I’m acting or forcing myself to be someone I’m not. The idea of outright flirting with someone or trying purely for sex feels sleazy and unappealing to me personally.

Am I wrong to feel this way or is this just because of my inexperience?

Another problem is that I’ve never experienced true love and I just don’t know how to flirt or initiate a romantic relationship with someone else. Whenever this topic comes up in conversation I kind of just freeze and completely blank. I struggle to start conversations with people without something concrete to go off and I work full-time in an office in a male-dominated industry so I find meeting people that I want to talk to really difficult. I mostly just want someone that I really like and respect to spend time with, where we can support each other in life and have ‘that look’ when we see each other.

I’ve just been feeling really empty recently and I don’t what I should do next. I feel like the clock’s ticking and I can’t afford to be stuck like this for a lot longer.