Ask A Very Smart Brotha: I Cheated On Him A While Ago, Should I Tell Him?

March 20, 2013  |  
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Jasmine: What is the most reasonable time period in which a woman should receive a proposal from her boyfriend?

DY: I don’t believe in an arbitrary set time for things like that. But, I will say if you’re in your late 20s and above, just “dating” for longer than two years probably isn’t the best look


Nita: Who comes first in your life, your wife or your mother?

DY: Wife. In my opinion, a wife comes before everyone else, including children.


Cynthia: Why do today’s men want women to take care of them?

DY: Men, by in large, follow the path of least resistance. Basically, (some) men expect women to take care of them because (some) women are willing to do it.

Source: Thinkstock


Shahdae: Is it okay to date more than one guy at a time?!

DY: Of course! Dating is supposed to be when you’re out meeting people and finding out what you like/don’t like and need/don’t need. How are you going to do that if you don’t date multiple people?

Source: Thinkstock

Yves: How do men know they are ready to have a child with a certain woman?

DY: Depends on the man. But, even if he doesn’t come out and say it (or believe it), “willingness to go raw” = “willingness to have children.”


Arhovist: When your man is being a jerk and. Drinking more lately but he says its because he is stressed with going back to school…etc. what is the appropriate time to let him know about his self? Or the correct way to approach the situation?

DY: Immediately


Hawoly: Is abstaining from sex until you find the right guy, my special someone, a good idea, or does it just scare guys away?

DY: It’s not a bad idea at all. And yes, it will scare some men away, but that’s kinda the point, isn’t it?

Kat: How do you convince a stubborn man that thinks he’s right on every subject that he’s not…is some cases, and how do you convince him that “your” opinion/feedback is just as valuable as his?? I mean no one knows everything!!

DY: Usually, you need to “show” stubborn people, not convince them. Basically, name a specific time when he swore he was right but was proven to be wrong. Also, stubborn or not, a person not respecting his/her mate’s opinions on things is a bit of a red flag.


Leah: How does one get a man, who says he has had his heart broken too many times to trust you, to be vulnerable with you?

DY: Be patient, and prove that you’re trustworthy. (Btw, a man or woman who can’t trust probably shouldn’t be in a relationship anyway)

Source: Thinkstock

Clarissa: If you cheat and know you made a mistake should you tell your man or take it to the grave?

DY: Honestly, it depends on when. If this happened some time ago—and you know it won’t happen again—I think you should keep it to yourself. But, if this happened recently, you probably need to tell him because your sexual behavior has put him at risk. He needs to know that.

Pittsburgh native Damon Young (aka “The Champ”) is the co-founder of the ridiculously popular Their first book “Your Degrees Won’t Keep You Warm At Night: The Very Smart Brothas Guide To Dating, Mating and Fighting Crime” is available at

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