During and after a messy break-up, I spent nine months without any intimacy. It drove me up the wall.

Four months later, I partnered in business with a guy. We became intimate. He knew I’d experienced two messy break-ups - one cheater, one needy guy - and I didn’t want a relationship.

I knew he had a girlfriend whom he cared for, but she’d withdrawn intimacy.

Our relationship is great, and honest. I want him to be honest with her because, as a victim of cheating, I know how damaging it’d be if she discovers him cheating.

I feel extremely guilty sometimes, knowing what I’m doing is wrong, though this relationship helped me regain self-confidence.

As I’m now seeing someone else, I cut off all intimacy with him, but we’re still great friends.

Is it wrong for me to ask him to tell his girlfriend about us? Our friendship might suffer, as I’ve met her and we might be seeing each other often.

I can live with the secret, but I know I’ll feel that little pang of guilt. Also, would it be wrong if I didn’t tell my guy about my friend-with-benefits? If I do, I should avoid saying who it is, as my friend will still be in the picture.

Multiple Awkward Connections

You’re a juggler of complicated relationships, which I usually tell people to avoid.

Somehow, you expect only a pang of guilt where others would be deeply anxious about exposure. You’ve found a similar spirit in your “friend,” who also rationalizes tangled relationships.

Will you both be able to keep your “secret” while he stays with his girlfriend and you get closer to someone else?

Who knows? But here’s what observing human nature has shown me:

Your previous unhappy relationships have given you a sense of entitlement, which, if it persists, will land you in trouble if you ever care deeply about someone for the long-term.

Most men do NOT take well to stories about old lovers. Most ex-lovers do NOT want their girlfriends to know they cheated.

Most relationships thrive on commitment, loyalty, and few complications. Cool emotional attachment to this friend.

This fellow and I got to know each other over the course of a year. I’m cautious about not jumping into a relationship. This was developing nicely, just getting to know each other.
After six months, I had a feeling he was holding something back. I really liked him so I just let it coast and kept him somewhat at arms’ length. Turned out he was married. Once I discovered this fact, he said he wanted more with me.
I said that he’d better think about what he was doing, and that he was about to lose everything and have to start his adult life over… meaning that, in a split, his wife would get half of everything he owned and she deserved it.
I was truly hurt. I didn’t want to start a relationship that way, and I had no desire to hurt another woman. Today, he’s a good friend and thanks me whenever I see him, for saving his marriage and his life.

My Bad Luck

I disagree with your “bad” luck. I think you’re fortunate to have been cautious in this relationship, to trust your instinct, and respond self-protectively.

You saved yourself months/years of being his listening post, as he alternately felt guilty and leaned on you, and perhaps never left his wife.

Or, he did finally divorce and you ended up with him as second prize.

I dated a girl I've known for awhile. We both agreed that we were everything each was looking for. She has great morals and values, with her priorities straight, which attracted me.

But a few days into the relationship, I started getting the cold shoulder. She said she wanted to do the best thing for her kid and that there was a lot of drama going on.

She said we should just be friends till things calm down, so we can start our relationship off right.

A week later, she hasn't talked to me, nor replied to texts. Should I keep waiting for her or just move on?

Fearing Heartbreak

Drama doesn’t end in a week. She has issues, perhaps her ex’s or her child’s reaction to her dating. Her priorities are still admirable.

Take a break for two months, and just send caring (not needy) texts, from time to time.