Dear Destiny, 

I’m weirdly attracted to my boss. She’s an older woman, but I just turned 19. It’s like there isn’t any age difference between us. We’ve been hanging out a lot lately after my shifts and I want to start this relationship. How do I go about this? – Strange Attraction

Dear Strange Attraction, 

No. No. No. No. And if I haven’t made my point yet, no. Honestly, I know that you are a grown person who can make mistakes, but I have to tell you this is a big one.

When I was a young teenager, I would say the ages of people that I’d be willing to date. For the most part, I would say one or two years but as I got older I moved the gap to around four. Now, as I approach the end of my college career, I restricted the age back to two. Age really isn’t a number and I know that mindsets grow a lot after college. 

Even throughout my college career, I’ve been amazed at the fact that I am basically a different person every year. The thing about maturity is that you don’t realize how immature you are until you get to another level of maturity. It’s easy to think you have all of the answers until you realize that you don’t. If you think you are mature enough for this person or this move, wait a year. I’m sure you’ll think differently. 

I don’t want to upset you when I say this, but you aren’t ready for this relationship. I don’t think anyone in our age group has the ability to have a meaningful and healthy relationship with someone in a radically different age group. I don’t know how old this “older woman” is, but due to the fact that you didn’t mention it I can already imagine the gap. 

I can’t discount the fact that this woman is your boss either. If you happen to set the age difference aside, the inequality within the relationship will get you. Your boss has too much power within the relationship. If she gets mad at you, she can make your work life a living hell. Maybe she can figure out a way to fire you. I know that you might argue that your relationship is stronger than status, but nobody knows what the future holds.

Are you willing to lose your job for this? And if you’re not, why are you considering such a dangerous relationship? 

The fact of the matter is that starting this relationship is ignoring too many red flags. I’d be a little more lenient in my answer if there was only one conflict within your relationship. However, there’s too many potential conflicts to ignore within this situation. I’d be lying to you if I said that I think this a good idea.

I know that this isn’t the advice that you wanted to hear, but I truly believe this is the advice you need to hear. Good luck, Strange Attraction. I believe in you. 



If you want to submit questions for Destiny to provide advice for, feel free to shoot her a message at this form.

For comments/questions about this story, email or tweet @TheWhitOnline.