Justin dear,
Lamenting about the past and chances we never took serves only 1 purpose. Of realising that which with appropriate tools we would have done different. Appropriate tools are: knowledge, confidence, trust, faith, and... to most of us they come with experience.
Like the wise man who got to be wise by making mistakes and learning from them. Like most of us past the year 42 of life ..lol.. the magic number. The secret of all that is: 42

(okay that was a joke if you remember the Hitcher's Guide to the Universe - however it was an uncannily true for me).
Anyway you start by relaxing

not as in becoming idle but relaxing your iner state - and that with the absolute knowledge of the spiritual law of the fact that you SHALL overcome what you desire to do so simply because you are 'asking' for it. It works like this.
We are given yearnings and desires because we "have" the potential to achieve them. And the next key word is action.
So to rehash what we said so far is this:
1. we have a desire
2. we reflect upon it by recalling everything possible that is in the way of fulfilment and taking measures to correct it ... a lot of times works best if you imagine the final state of that that you want to reach and working backwards.
I.e. you fancy a girl that and you lost your chance to be with her because at the appropriate time you were much to chicken to approach her, or perhaps it was to early to even realise that you wanted to be with her - a lot of times we have no idea what we want and we get an inkling only after we miss that chance - anyway "now" you 'think' about it and imagine yourself with her in the most intimate and soul closeness situation/state , this will get you over the scare of daring to be / talk with her in all possible open upfront manner very much as you would talk to yourself. Then you think how you got there, what happened 1 day before you got there, then 1 week before and so on until you get back to where you are right now however the difference is that by now you did the mind exercise and got some 'ideas' on how to proceed.
so far this all happens in Mind
next comes
3. Action - which has 3 elements: (a)self-education, (b)mock-practice and finally (c)practical application
(a)Perhaps you read a book on 'mastering conversation', or 'the guide to building confidence in approaching future relationships' etc etc... A friend sustains that is not admissible that today with so much information and knowledge to stay ignorant about these things. Justin, I was 42 when I realised that most of my mistakes were done out of ignorance and you may laugh however I got this online book entitled something like "get him and keep him" ..lol.. i can't even remember however that opened a can of worms because I become even more hungry for knowledge into relationships, how people's minds works, how men think, how women think, why people behave the way they do etc... in time I realised I was looking for answers about myself.
(b) while educating yourself go out and practice all newly found skills, approach people, talk get involved in physical stuff where people mingle remember that's why there r so many individuals in life so we get to practice in a live simulation that which we become. Don't be scared of mistakes, awkward moments - we all have them - get over ..keep going at it and in time your self-confidence will soar unbelievable limits. So in this respect (b) and (c) may be same the important thing to keep in mind is that there r no mistakes only experiences - something we learn integrate and don't repeat if they didn't got us the desired result.
So when you say you are scared of love I assume is the romantic, passionate kind. Which is a guide towards the unconditional love because as we feel when in love that's how we should feel at all time towards all people, life ..creation. Read this again (
http://www.astrodreamadvisor.com/M_yellow_elec_sun.html) perhaps it gives you some insight on why love scares you. Ask yourself - okay I express love what's the worse that can happen? Rejection, ridicule, loss?...of what? ... continually reflecting on such questions you will realise is only Ego talking (Ego protects you it doesn't want you to risk yourself..) What do I have to loose, and if I loose ..so what?
Then again remember you are young, you can afford to make mistakes, learn start over etc... after all that's why you live. Is an adventure!!

Look forward to all challenges knowing that they only exist because we set them so in order to be able to rise above.
Anyway you may also want to look into some training on being assertive, and building self-confidence etc... Bit by bit they help... you have no idea how much!!

Good luck and love