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Sam: Since you are halachicly obligated to get married by age 20 according to the Shulchan Aruch (or according to some shittos by 24 if learning Torah full time) then you can’t start getting into the shidduch parsha for the first time at 19.5 and six months later say, hey, I tried. Obviously you need to give yourself enough time prior to the halachic deadline age to be married by so you can comply with that halachic obligation of yours. If it is reasonable to expect to find a shidduch within one year of starting to look, you need to look at least one year before you’re required to be married by. If, as more likely, you can reasonably expect the search might take longer than a year, then you need to start looking at least that much earlier.