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Is Complication A Deal Breaker?

Dear Sugar
I have been working with a girl over the past seven months, that I have really grown to like in a romantic way. She has a very complex past which is the only reason this situation is problematic. She is 22 years old and just had a baby with a man who wants nothing to do with her. They are still working through their breakup and I know this hasn't been easy on her.

I think about her all the time and can't deny my feelings anymore. I know she isn't looking for a relationship right now but is it worth taking a chance and telling her how I feel? If we were to start dating things would be quite complex. Should I knowingly sign up for this challenge, or should I just keep the relationship in the friend zone? Conflicted Christopher

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Dear Conflicted Christopher
Timing is everything when it comes to making a relationship work so if you know your work hottie isn't ready to be in a relationship, you might want to hold off expressing your feelings until her life is a little more settled. It sounds as though your crush could use all the support she can get so be her friend and see what happens.

If you still can't hold back your feelings and decide her convoluted life isn't too much for you, try saying something like this that is to the point but will not make her feel pressured:

"I know you are going through a lot right now and I don't mean to complicate matters even more for you, but I have to be honest and tell you my feelings for you have developed into something stronger than a friendship. I just wanted to let you know in case you were feeling the same way."

Keep in mind that your crush has her hands full with a new baby and a fresh breakup, so be prepared if she still isn't ready to date again right away. If you sense hesitation in her reaction, tell her that you are willing to take things slow. I hope it works out for you.

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