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Why Do I Lose At Poker? The most common reason that you are always losing when you play poker is that you are playing in to many hands. If you look at any two pocket cards and add a little imagination you can make a good five card hand out of almost anything. Is it going to happen. sure it is but is going to happen such a small percentage of the time that you will always loose in the long run if you play these hands. Try playing only, what I call the blackjack hands the next time you sit down to the table. These are hands that add up to 20 or 21. Aces are 11 and face cards are ten with all the other cards their stated numerical value.