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Step 1
NO SHENANIGANS ATE WORK. Leave all of the flirting and other antics you can think of out of the workplace. If you can get away with it, meaning your boss is sort of like another coworker/friend then whatever. But most of the time, this is not the case, and you don't want to risk anything. I'm not saying don't talk to each other and give each other little flirtatious looks, but don't do anything beyond that.
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Step 2
DON'T PUT HIM BEFORE THE BOSS. If you know that refusing another overtime will result in a possible termination, and you really want to skip that overtime because you want to be with HIM, then you need to get your priorities straight. He is not working for you, you are. He is not paying your bills, you are. He is not your boss, your boss is. Nothing is that important to where you're going to risk your job to spend time with HIM.
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Step 3
DON'T PUSH THE BOSS IF HE/SHE CAN'T PUT YOU TWO IN THE SAME TIME SLOT. Don't annoy the boss with ask him/her to put you in a specific time slot the would make you see your coworker more. If the boss can, fine. But if the boss needs you for a specific time that does not coincide with your coworkers time, THEN LEAVE IT ALONE. It really isn't that big of a deal. You might get your request, but it will be outside of work with you having no job.
