Life Advice



Fool Me Twice, Shame on Me

Annie Lane on

Last year, she cheated on me with her ex. She broke it off with me and went back to him. They had problems, and we recently started talking again. She wants it to be casual and see what happens. We have sex and everything, and I'm starting to have feelings for her again.

She has said she misses the things we used to do and sends me kissing emojis when we text. I think I see signs of her wanting more, but I'm not really sure.

What do I do? I want to bring it up, but I'm afraid to because I don't want to ruin it if there is a chance. Casual dating and I don't mix too well. I want and need more than casual. -- Cautiously Optimistic

Dear Cautiously: You can't ruin something you don't have.

Now's the time for a serious conversation with this woman to see what she's looking for and compare it to your expectations for the relationship.


If you want more than a casual thing and she only gives you loose answers and no commitment, you're just setting yourself up to be more disappointed and hurt down the line the longer you stay with her.

And on the point of commitment, don't forget she has already been unfaithful to you once before. As Maya Angelou said: "When people show you who they are, believe them the first time."


"Ask Me Anything: A Year of Advice From Dear Annie" is out now! Annie Lane's debut book -- featuring favorite columns on love, friendship, family and etiquette -- is available as a paperback and e-book. Visit for more information. Send your questions for Annie Lane to




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