But what is the Catch 22 of dating? Well, a desirable date is someone who is fun, outgoing, and has an active social life. But someone who is looking for a significant other may be lonely... which is why they are looking for someone. Especially after a break up, it can be impossible to pull yourself out of a funk and go out and have fun again. But the dating pool doesn't exactly reward these individuals. Without interesting friends and hobbies, it's hard make conversation!