Relationships Talk

Now comes the hard part: You have to decide whether the benefits outweigh the risks. If you’re seriously worried that flirting with an old boss could harm your career, then don’t chance it — there are plenty of other amazing people to have amazing sex with, date, or marry. But if you don’t think asking for the date will make any difference to your current or future jobs, then why not? If that’s the case, asking out your ex-boss becomes just like asking out any friend or acquaintance. Sure, it’s still hard, because facing rejection always is, but it’s 100% doable.