I'm sorry you feel so lonely. Unluckily, I believe while you feel that way you are not in the best position to attract others: they sense your deep need and a sort of void they feel inadequate to fill themselves, so they stay away.
I would suggest you begin by trying to fulfill yourself through doing things you love, if you have the time. Once you are felling better with yourself, you will look like a more independent and interesting person in whom others may sense an interesting exchange, rather than having to take up the role of comfort givers.
I know this advice is easier to give than to follow, but I have found out that whenever my moods are swinging, I am not fit for company, so I take refuge in my interior designing, my books, Tarot, this board... Till I feel once again I am ready to deal with others.
Fear of rejection is strong in all of us, so we must have a B plan in case it happens. That is, imagine being rejected and feeling not so bad about it, more an attitude like 'So what?' or 'He's the one missing out on a good thing'. Approach it like you have nothing to lose because that's the truth: if you never try, you already have the NO.
Also, you can work it in such a subtle way that, if he shows no interest, you can always fall back on your friendship with him and keep things smooth, trying to spare you both an awkward moment as much as possible. A light, joking mood is usually my own way to tackle these things when I am not sure of the outcome.
Hope you can make use of some of these ideas. I know you will feel better in no time. Big hugs
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