Delphina Boncompagni Ludovisi

November 02, 2011

Dear Delphi,

I broke up with my daughter’s mother over a year ago, but I have been over to her place a few times and have slept with her. I love my current girlfriend very much and I have mostly stayed away from my ex, but my ex has said that she is going to talk to my GF and tell her everything. What should I do?

—Cheating With My Ex

Dear Delphi,

Can you help?

While on holiday earlier this month I bumped into a girl who is the ideal candidate for an affair—she’s hot, sharp, and dry (sounds more like a bottle of sake, I know). We’ve hit it off before but haven’t seen each other for a while.

I am happily married, but the occasional weekend of guilty pleasure with this chick would be fun. This assumes that she is looking for something on the side. I think she might be.

“If you are not man enough to live with the guilt, then you are not mature enough to cheat.”

There are obstacles to an affair:
1) She is married.
2) I am married.
3) We live in separate countries.
4) We have friends in common.

My questions:
1) Is it acceptable/sensible to attempt affairs with a married woman with whom I share mutual friends?
2) Do a long-distance affair’s logistics remove spontaneity or merely make this more thrilling to pursue?
3) Logistics aside, do you suggest I visit her for an illicit weekend?
4) An affair on holiday might have been a better option, but it didn’t happen, so how do I get this thing started now that we are so far apart?

—Affair Candidate