My Boss' Daughter

Dear Adam,

I am 17 years old and I work for a man who is in the importing business. He has a daughter a couple years younger than me who is quite pretty. I don't want to mess up my summer and after school job by dating his daughter, whom has not be on a date yet... however, I have lived so close to her for so many years and I just can help but wonder what it would be like if she and I were together. What should I do?

Sincerely,
K. Ray

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Dear K. Ray;

Thank you for your question. I agree that it is difficult to date the bosses daughter, even if she is quite attractive. However, if you follow your heart but keep all the factors of life in mind then you will reach the right way to go.

It isn't so much about whether you should date her or not, but rather whether why you find her attractive at all. Think about what you will think in 10 years. Will you regret not pursuing your boss' daughter a little more? You could always take her out for ice cream or something very mild like that until she feels comfortable doing more date-like activities.

And so, bear in mind all possible out comes and if it is something that the pros outweigh the cons, then go for it. If you still feel uneasy, then perhaps you can find someone else to think about.

Hope this helps.

Yours,
adam