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The point is: that year, I ended up in a charter school program that had me taking classes at the local community college, which was terrifying after years of studying alone. For the rest of the semester, I’d stare at him longingly through class and think of him around the clock despite knowing I’d never work up the confidence to speak to him myself. I knew no one in the class and spoke to no one on campus. At the time I was proud of myself for being ready to stick to my guns and turn down a group sex encounter with the best-looking person I’d ever seen.

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Just like how you’ve dated your share of challenging types of men like the Pinger, the Couch Potato and the older-and-balder-than-his-profile-guy…men also meet and enter into relationships with less-than-impressive types of women.

I’ve talked to countless single men over the years about their experiences with women, especially those in their 40s, 50s and beyond.

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Karissa Schaper, 27, of Madison, homeless for the past decade, reacts to seeing her new studio apartment for the first time at the new Rethke Terrace housing project for single homeless adults and veterans on the East Side.

People ask me all the time whether I offer dating and relationship coaching for single men. But I tell them that I help men by helping women who are dating after 40. ) One of the most transformational ways I support women is by helping you better understand GROWNUP men.

Just like women, the men you’re dating have lived and learned.