Starting Off
Try attacking a puzzle in a group. Different people think differently and approach things differently. If each can get one word which is stumping the others, you all have more to go on with the extra letters in unknown words. And the whole competitive thing can be a real spur to getting the brain working.
Start on good quality crosswords. A cryptic clue can be like an adult joke, or a 5 year old joke. You might get the latter but you wouldn’t want to repeat it. Unfortunately, I class the Age/SMH compilers - with the exception of David Astle (DA) on Friday - as run of the mill. On the joke scale they would be about Benny Hill. But in their favour they don’t often break the rules, so at least you know they’re not leading you astray. David Astle is definitely in Billy Connelly’s class.
If you get the chance, look at the London Times Crossword in The Australian - that is where I and my friends started all those years ago, and it is the one I still do. Be aware that they have a stable of compilers and the degree of difficulty varies from reasonable to diabolical, with no indication of the compiler. (I have found out that those who do the crossword in the Times do have an indication of the difficulty of each one. They range from easier on Monday to very difficult on Friday, with the Saturday Prize crossword somewhere in the middle. Because The Australian publishes at a variable date behind - usually about a month - you have no idea of which day it was originally published. But as you get into solving you may think ‘Oh, this must be a Monday’ or ‘Ah, a Tricky Thursday’.
Another good source is the free online offering from the Guardian. They have a large number of setters, all named, of varying degrees of smart-arsedness. There are three advantages of this site. Firstly they have a large historical collection so you can try multiple crosswords a day if you get obsessed. Then you can check an answer. This will delete all letters which are not correct. And if you get really frustrated you can reveal an answer. This can give you letters in unknown crossers to help you on your way. Go back over the crossword with the published solution and try to work out the answers you didn’t get. Once again this is a good group activity. There will be some clues which you still can’t fathom, even with the solution. If you have a good compiler, it is most likely that words have been used correctly in a sense foreign to you. You could try further research. For Times solvers there is a daily blog which parses each clue. Even then I sometimes find the explanation doesn’t leave me any wiser. The site can be accessed at crosswordclub.org/tftt/showlinks.php. I don't know of a similar site for the Guardian but there may be one. There is a site DA Trippers dedicated to David Astles crosswords. Get a good dictionary/reference and a good thesaurus - online or hardcopy. An online dictionary with search capability can be very handy. Also an anagram program . I don’t think using an online dictionary search in solving is cheating - you still have to be able to pick out the correct word from the list generated. And it is a lot quicker than a manual search. If you are on your own it can provide some of the benefits of working in a group. Also, one of the real joys of a cryptic is to work out a word you have never known before. Finding it in the dictionary, with the meaning you hoped for, can be a real buzz. I can still remember the first time this happened for us. We were stuck on the clue ‘Has the lady visited a speakeasy? (7)’. I can’t remember what sequence of letters we had, either -h-b-e- or s-e- e-n. Then suddenly one of the group exclaimed ‘She been?’. When we went upstairs and looked up a dictionary there it was: ‘Shebeen - an unlicensed house selling illegal alcoholic liquor, esp. in Ireland’. You are not going to find uncommon words in a basic dictionary.
If you find yourself completely stuck put the crossword down and do something else - even to the extent of going to sleep. It is a well known phenomenon that our brains continue to work on problems subconsciously. Quite often you will come back to the crossword and immediately see connections that eluded you before. I have often gone from a half-completed puzzle (which I had spent a long fruitless time on) to completing it quite rapidly the next day.
Another good source is the free online offering from the Guardian. They have a large number of setters, all named, of varying degrees of smart-arsedness. There are three advantages of this site. Firstly they have a large historical collection so you can try multiple crosswords a day if you get obsessed. Then you can check an answer. This will delete all letters which are not correct. And if you get really frustrated you can reveal an answer. This can give you letters in unknown crossers to help you on your way. Go back over the crossword with the published solution and try to work out the answers you didn’t get. Once again this is a good group activity. There will be some clues which you still can’t fathom, even with the solution. If you have a good compiler, it is most likely that words have been used correctly in a sense foreign to you. You could try further research. For Times solvers there is a daily blog which parses each clue. Even then I sometimes find the explanation doesn’t leave me any wiser. The site can be accessed at crosswordclub.org/tftt/showlinks.php. I don't know of a similar site for the Guardian but there may be one. There is a site DA Trippers dedicated to David Astles crosswords. Get a good dictionary/reference and a good thesaurus - online or hardcopy. An online dictionary with search capability can be very handy. Also an anagram program . I don’t think using an online dictionary search in solving is cheating - you still have to be able to pick out the correct word from the list generated. And it is a lot quicker than a manual search. If you are on your own it can provide some of the benefits of working in a group. Also, one of the real joys of a cryptic is to work out a word you have never known before. Finding it in the dictionary, with the meaning you hoped for, can be a real buzz. I can still remember the first time this happened for us. We were stuck on the clue ‘Has the lady visited a speakeasy? (7)’. I can’t remember what sequence of letters we had, either -h-b-e- or s-e- e-n. Then suddenly one of the group exclaimed ‘She been?’. When we went upstairs and looked up a dictionary there it was: ‘Shebeen - an unlicensed house selling illegal alcoholic liquor, esp. in Ireland’. You are not going to find uncommon words in a basic dictionary.
If you find yourself completely stuck put the crossword down and do something else - even to the extent of going to sleep. It is a well known phenomenon that our brains continue to work on problems subconsciously. Quite often you will come back to the crossword and immediately see connections that eluded you before. I have often gone from a half-completed puzzle (which I had spent a long fruitless time on) to completing it quite rapidly the next day.