Needed to Rant...

So, I have been having the same conflict for a while but the past few months it has really been getting to me. I think the fact that it has been an issue for so long and is now becoming I can't ignore or push aside is interesting to me...why now?
My conflict is hard to explain I feel, not sure what category it would fit under, but I have low self-esteem issues and that seems to have always been a part of my problem, which is finding someone who would desire or cherish me...in a sense. I am tired of being alone, and when I say alone I mean a virgin who has never slow danced with a guy, had a date, kissed or even widely flirted.
I reach a low about this ever month, probably a part of my cycle which is a part of my diagnosis (PMDD Pre-mesntral Disphoric Disorder) and just seeing sexy pictures of what desirable woman look like seems to add to it. I have never been more aware of the constant visuals of ideal feminine beauty, which is highly unrealistic to me. I am pretty overweight and am trying to be healthy, working out and watching what I eat, but even if I got super serious about it, that ideal isn't in my reach. I feel so hopeless and alone not in the sense that I am the only one that feels this way, but that no one has loved me that way, or at least been attracted enough to me to do something about it.
I feel like I have put myself out there, I can always try more, but even when moved to change and I act on it, nothing budges. I have been this way for so long and all attempts to change it have not really panned out leaving me even more hopeless about it than ever.
My friends have always told me I am such a good person, that I am actually not that bad looking and the kill shot, I just haven't met the right person. But to hear that as well for so long with no inclination of truth I have seen to prove it just frustrates me further.
I haven't felt this low about it since High School really and there are probably many reasons this is happening now, but this is a low I don't want to be in anymore, it is a path I don't want to stray on.

I get the feeling that the first thing you want from a boyfriend would be to affirm your desirability and value as a sexual being. What about just finding a male friend or exposing yourself to male company? That would be a pretty good first step for you.

You've mentioned this before. You seem to get very upset over glamourized portrayals of relationships, women and lifestyles.

I laugh at pictures of afghan hounds lying on chaise lounges with throw pillows and hardwood floors in glamour magazines, as I realise that these are shots manufactured by photographers. They don't depict reality.

It's the same with the models. You don't have to live up to pictures of models in magazines because they are unrealistic portrayals of normality. Pictures which are airbrushed and often unattractive anyway.

Maybe it's not a matter of effort, but your approach. Too much effort smacks of desperation, and that's never attractive to anyone.

Ask them to hook you up. Or if not that, to expose you to the company of eligible males. You don't have to go out with them, just chat, mingle, and open yourself to the possibility of flirting or being flirted with. That would be a big first step.

Totally different reason to rant today. Instead of being moved to tears about being alone and all the issues I have around that I just feel kind of resigned to a dull, uneventful and unsuccessful life.
I don't see much of a future for me (and that isn't a mention of suicidal thoughts, it is an explanation of how I a feeling right now which is no where near that). What I mean by no future is I have no drive to go after a career that is either one I would enjoy or one that is financially successful. I don't see me finding someone to share my life or having a family of my mom, I more see myself as a sidebar to my immediate family or now my brother's new family. I am the one to take care of the parents in their old age, to babysit my niece and kind of just be there for others rather than living my life for myself.
This is a tricky area, because I like to be needed and actually am thrilled about becoming a Aunt but it almost feels like that is the role I am stuck in or taken for granted for. I don't see any big milestones in my life to strive for, celebrate or look forward to, just endless days of working and uneventful weekends. Even traveling doesn't seem as appealing as it used to be, because with no one to really share it with it kind of puts a damper on the whole idea. I feel like my achievements peaked in college but after that path ended I was left kind of hanging in the middle of nowhere. Not knowing what my next step was or what I would want it to be or lacking any motivation to figure it all out, let alone begin to follow a different or new path.
For some reason, all of this isn't really making me feel depressed, instead it is more of a realization, all-be-it a sad and pathetic one, but it is almost comforting (even if twisted) resignation.