Ask Chad: Dating Advice, Flakes, and Bottoming 101

Good morning holes and poles, raise your hand if you need a tequila soda right now (I’m raising both hands!). March has been one word, HORNY. My hole is literally insatiable as I’m coming out of Winter hibernation and springing into the sheets!

Dear Chad,

I am a little annoyed to have to even ask this but what is the policy on paying for dates? I recently went out with a guy for the second time now and I had to pay for everything BOTH TIMES. He didn’t even reach for his wallet when the waiter brought the bill, or when we went to the movies! I feel like that’s so rude—like it should be his turn the second time right? Or do I have to say something about splitting the bill from the beginning? 

Thanks,
NotUrSugarDaddy
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Chad,

There’s nothing that ticks me off more than a flake, and lately, I keep getting ghosted on the apps. I get tons of messages when I first log on but by the time I am ready, or the later it gets, the more likely they are to flake on me and then I end up finishing myself and going to sleep. How do I get a hookup to come through?

SOS,
Night Owl

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Hey Chad,

I am typically a top and have limited experience bottoming, and the reason is that it hurts too much. Every time I go through the same thing, clean out, hype myself up, poppers, lube, and try taking it slow. But the outcome is always the same, it hurts and I can’t enjoy myself and then stop him after a few minutes because it is too unbearable. How do I bottom without it feeling like I’m passing a watermelon?

Thanks,
Novice Bottom

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Keep your questions coming! Nothing is off-limits! Email me: [email protected]. Until next time!