adjacent advice: if you need more confidence, get a cool jacket or a haircut or something and think about how cool it makes you. this is loser advice, but we're all losers here. swallow your pride and roleplay as a cool guy and you'll become a cool guy.
Back in 1066 if you were out of cash you could just go to a castle by the sea and pretend to have washed up and say to the lady when she finds you in the morning “verily was my vessel thrashed uponne y rockes, and was I threwn theroute, and nighly drownèd, but spied I a maiden seated on a cresting waive, and she spoke unto me thus, Thou shalt upon a new land happen, and the Ladie who ruleth there will do good unto thee, and robeth thou in the coloures of her house, and take thy hand in marriage upon y dethe of her Lord, and then that sea-maid sung an a daulphin issued me from y tempest to this gentle cove” and she would just believe you. And then when her husband died the next day of “stomach upset” she would marry you and you’d be fine. It happened so often