Should I let him know he has no game?

Anonymous
One of my friends set one of our guy friends up with this girl who we thought had a lot in common with him. But she sent us and another huge group of people their entire texting conversation and it was bad. It was extremely cringy. He's seems extremely desperate for a relationship. So should I tell him he has no game or just let him continuously wonder why he can't get a girl.
Should I let him know he has no game?
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