I’m on a management team at work with several people. I've started sleeping with one of my peer’s ex-girlfriends and he found out about it from mutual friends.

Their relationship of two years was serious, but it ended eight months ago.

He’s expressed sadness and anger about the situation to friends. I had no idea it would affect him so much.

So for now, out of respect, and for work purposes, I’ve stopped all interactions with his ex.

Am I in the wrong for getting involved with this woman? Should I have done more to hide this fling from him, for the sake of not hurting his feelings?

Feeling Guilty

Yes to your first question, and No to your second.

Had you said that you and this woman were drawn to each other and fell in love, and then I’d say, “Well, these things happen.”

Then I’d say, you should’ve told your colleague about the mutual attraction yourself.

But you’ve written of only a “fling,” and of sleeping with her – both facts conveying no strong emotion.

In that case, there’s the same unwritten but well-known “rule” to not mess around with a close friend’s, or a close colleague’s, once-loved ex. Especially during the first year after they’ve split up.

However, my “No” applies to hiding the situation better. That’s not a stand-up guy’s solution, and it only looks worse on you when discovered, which almost always happens.

Apologize to your colleague. And to the woman with whom you could have sex, but not enough caring to handle this better.

I'm 21, male, and the only relationships I've had have been online and both ended horribly with me being cheated on.

I want to start dating in my area, but I'm extremely shy.

I've been highly sheltered (not by choice) with my only interactions with people being at school or church.

I have a stutter that I'm trying to overcome. The only time I feel confident enough to talk to anyone is when someone cares about me.

I've been going to a weekly college club hoping to meet new people, but everyone there is either already dating someone or I'm too afraid of coming on too strong.

There’s a masquerade party coming up and I don't want to go to another couples’ gathering alone.

How can I get over my fear of talking to girls and ask them to go with me, without coming off as over-eager?

Inexperienced

There are lots of young college students who are also lacking confidence for one reason or another.

You need to take one step at a time without over-thinking each move.

Go regularly to the club, talk to anyone who presents as friendly. Start looking for casual acquaintances, male and female, instead of dates.

It’s through these new contacts that you find out who’s already attached, and also who has a female friend who’s open to meeting someone new.

When you do meet an unattached young woman, ask about getting together for coffee, instead of directly asking for a date. You need at least one opportunity to just chat together.

The stutter likely gets more pronounced when you’re nervous. There are methods for treating this which you can look into, but meanwhile try to stop seeing dating as a one-shot goal that you either pass or fail.

Things will get easier once you stop seeing socializing as a mountain to scale, when it’s really a path to take gradually.

Whenever I say anything to my sister (three years older than me), she’ll tell my mom but twist it into something worse.

My mom will punish me for it, whether not hearing my side, or hearing and not caring.

When I once snitched on that sister, my mom said to forgive her.

I’ve tried ignoring my sister, but she’ll still push me around which gets me so angry.

Our oldest sister (five years older than me) is the peacemaker, but she’s soon leaving.

I feel bullied by my older sister.

Troubled in Tanzania

Find a time when your mom’s not too busy and when there’s not been a sibling fight.

Then tell your mother how you feel in general about being “bullied,” and your concern for when the peacemaker’s gone.

Ask what she suggests you can both do to improve things, and ask for her help.

Meanwhile, no snitching. And no telling Sis what you don’t want repeated.