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I have 2.
1. Getting a joint account with my gf while in service to pay for our apartment without having to jump through hella hoops. After 2 years home I'd lost my job to a project shut down. 2 years I carried her with no job and no want to get one. A month after losing my job she leaves me, claims to my medieval combat organization I raped her, drained our joint account for the $6,000 I had in it from my tour and sold MOST of my memorabilia (medals, uniforms, etc) to a local surplus shop.
2. Investing $200 in various crypto and not cashing out when my portfolio was worth $100,000 before the bull run. I held and now I'm just waiting for it to all die so I can stop watching it slowly bleed out.