Dear Carolyn:
I met a guy in 2011 and we fell madly in love. At the time he had a girlfriend and she was pregnant, but I was OK with it! She found out and started sending me insulting messages to which I never responded (except once when she mentioned my mother!)
At the end of 2011, I broke up with the guy because I wanted him to be a good father and boyfriend to the baby and lady. In 2012, the lady befriended me and we sort of became close. I’ve always had contact with the guy, and he promised me that one day we will be together.
Now they broke up and the guy asked me to give our relationship a chance. How and when do I tell her I’m planning on giving my relationship with the baby daddy/ex-boyfriend a chance?
— S.
You tell her as soon as you’re ready for her to dump you — and to recognize you befriended her as a convenience while you waited for her child’s father to come back on the market.
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I suggest also waiting until you’re ready to see that, even though she obviously has or had some maturity issues of her own, her dim view of your character will be dead-on accurate — that is, if you proceed with your plan to claim the spoils of not just waiting for this little family to fail, but also actively helping it fail by staying romantically in touch with this (choke) “baby daddy” throughout. (Since when did noncommittal parenthood become cute?)
So when you’re ready to face the reality of being that person, then go for it. If you’re not ready, then please take a hard look at who you’ve become, and how you can turn that around.
Dear Carolyn:
Is it ever permissible to comment on how nice a woman’s breasts look, especially when about three-quarters of them are exposed with low-cut dresses or bikini-type tops? (Single gals only.)
— D.
No.