Forcing a draw when you're losing

I was playing a game yesterday where I trapped and captured my opponent's queen. After that, my opponent started mercilessly checking my king on every single move (I did proceed to win by resignation though). That's when I thought of something— if you're in a losing position but you have many checks available, can you force a draw by the fifty-move rule? I've drawn by the fifty-move rule once; it was when I was playing the boxbox bot and it didn't know how to checkmate me with a king and a rook so it kept checking me.

Yes it is possible, but not necessarily always possible.

I'm not sure. By "a losing position", I mean a position where for example you have just your bishops and two pawns while your opponent has their queen, rooks, a knight, and many pawns. In that case you'd obviously be losing. If your opponent left their king out in the open, you could keep checking the king with your two bishops.

If they can escape the checks, then it is really a losing position for the weaker side. If not, then it is not.

Just because someone is down material, it is not a "losing position". A losing position is when you are losing.

In a position with perpetual checks, it's far more likely to get 3x repetition. I can't really imagine a situation where you get to 50 moves without repeating.

Not all that uncommon, mainly with a queen delivering a perpetual in a far advanced endgame. In an open board position there are many different places where the king can go and the queen can check from varying angles. Magnus had one in the (I think second last round of the) Tata Steel tournament of 2023. He agreed to the draw immediately as he saw there was no escaping his opponents queen checks. Note that the 50-move sequence can contain one repeat for each position without drawing. Also the opponent might have a piece like bishop or rook which occasionally interposes the check without stopping the perpetual - which resets the repeat counters.

But it is true that the 50-moves rule is more commonly triggered in positions where it is hard to make progress and where the checks are not all that relevant.

The fact that I find most fascinating is that Prawnydagrate has heard about the 50-move rule (which is probably the most obscure rule in chess that almost never matters), but did not hear about perpetual check. Really weird.

It means he is well-educated "Perpetual check" is a strategic concept but is not part of the laws of chess. In old versions ( I saw one from 1977) it is mentioned as an example to (if I recall well) the 50-moves rule but not as a distinct rule.

Well, there are a lot of things that you can't find in the rulebook (like fork or exchange sacrifice or smothered mate of "knight outpost" of "blockaded bishop"), but these are well known concepts that are useful and good to know. On the other hand, you can play for decades and never encounter a position where the 50-move rule matters.

The 50-moves rule has become much more relevant over the past decades by the discovery of all the tablebase endgames requiring more than 50 moves. I do not know about the statistics but I expect that many IMs and GMs will make an effort to win such endgames now where they would have aborted with a handshake in 1990. And the weaker players are already wrestling with K+B+N vs K or K+Q vs K+R.

When a person captures a pawn/piece, or makes a pawn move the counter is reset. What is it reset to? 0, and the 1st is the next persons move, or was either of those the 1st move?

I've heard of it, but I never learned what it meant. I googled it and sort of understand now. Perpetual check leads to a draw by repetition or by the fifty-move rule

Is this some trolling or what? None of this makes any sense.

Did you play against a computer or a rated game? Did you mate in 3 moves or did you resign?

I just realized there's a fifty-move rule and a seventy-five move rule and found upon research that the fifty-move rule only applies when a player asks for a draw by the fifty-move rule. When I drew against the boxbox bot as mentioned in the first comment, I was confused why we'd made fifty fullmoves with no captures or pawn movements and the game kept going. A long time later the game ended by the fifty-move rule. I'm pretty sure it was the seventy-five move rule at play here, because no player claimed a draw and fifty moves had already been passed without captures or pawn pushes, however the message showing the game had ended said "Draw by the fifty-move rule". I'm confused.

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What you say about the fifty / 75 rule is true, but over the board in real life. It does not apply on chess .com  or other sites that I am aware of. Along with providing notation online sites also appropriately ends the game automatically for you. While the 50 move rule does apply, you never make a claim, this site does it automatically. Further more you speak of BOT BOT, yet I am unable to find this game. The one which I believe you may be referring to  (apologies, My mind is a bit fuzzy and I m going off of memory which is short) round 65 moves on the 23rd. That game ended in a draw due to a stalemate if it is the one you are referring to. If it is another please due provide a link. Also the 50 move rule meas 50 moves per side, or 100 moves total.

Obviously, the next 50-moves series without capture or pawn move does not start with a capture or pawn move. So the reset for the 50-M counter is to 0 and not 1.

Which is different for the repetition rule because it is about positions not moves. Once you play a capture or pawn move you can no longer repeat any earlier position but the new position can be the first one for a different triple repetition!

Almost everything anyone has written about the 50/75-moves rules or the 3/5-repetition rules is complete nonsense. Even worse is what chess engines make of it. 

For instance, as a spectator can you walk up to the players of a game and tell them they passed the 75-M mark? Correct answer: Yes, you can though it is not necessarily polite. Why? Answer: The  game already automatically ended when the 75-M event occurred. There is no longer a game, there are no game players, there is no arbiter, and none of the game rules apply. Whatever you say is merely making conversation which may or may not be appreciated by the former players.

The way to handle such things would be to define some sort of meta rules relating to the context of the game. Like the arbiters might be instructed to protect the players from interventions as part of the competition rules until they signed the score sheet. But that's not FIDE chess laws! The game is over, not the competition!

Another example: After the 75M  mark has passed, someones flag falls or someone resigns. Does he lose? Answer: Of course not! Why? There is no longer a game going on to which the resignation or flag fall applies. The game has already ended in a draw even when the former players didn't know about it. Is this weird? No not even vaguely. It's the same as that you can't resign after you checkmated your opponent! The game is over, nothing left to resign about. It is still possible to sign the score sheet though with the wrong outcome, 0-1 instead of  1-0. Would that count as "a change of mind" or as "fraud"? Whatever, the answer is the same after checkmate as it is after a 75M event!