Problems with dating your boss

(By the way, he points out, that probably includes HR in almost every case.) If you opt to prohibit dating, Segal says, there’s one important thing to do before implementing the policy.Check out your senior managers to see if they have a history of dating employees.“Other than that,” says Segal lightly, “asking for dates is risk free.” In your training, he suggests, stress that when people are in boss-subordinate positions, even attempting to date is risky—it gives a club to the subordinate that he or she can use down the road.“My recommendation,” Segal says, “is to dissuade.” Some organizations require that managers and supervisors report to management before they start dating, he notes.

It has fostered suspicion among my peers that our compensation is impacted by this relationship.

We don’t really have an HR department, and I haven’t been able to find a policy listed anywhere that addresses workplace relationships.

Is it selfish to broach this subject with my co-worker? Since things have been strictly professional between the two of you, blindsiding her with a declaration of feelings is a recipe for awkwardness all around.

I don’t want to put her in an uncomfortable position, especially if I’m wrong about her returning my feelings.

On the other hand, I feel like I will regret it forever if I don’t ask her out, or at least talk to her about how I feel.

Search for problems with dating your boss:

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If you don’t see those things, that means you’ll need to back off.

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  1. Dave says, "Personal finance is 80% behavior and only 20% head knowledge." Even though your choices landed you in a pile of debt, you have the power to work your way out! The solution isn’t a quick fix, and it won’t come in the form of a better interest rate, another loan, or debt settlement.