Scrolling through Tinder, I see this hot girl and realize that it’s my coworker’s 18-year-old sister, who I know for a fact is a high school senior. Like WTF?! So I swipe right and ask if it’s her. We start flirting and it’s on. She asks when I’m going to ask her out. I invite her to my apartment because obviously we can’t go out. She comes over and she’s really into me. Bottom line: We hook up. And that’s what we’ve been doing ever since. Now I’m a 28-year-old loser because I’m dating an 18-year-old girl and can’t tell anyone. Any advice about how to handle this?

Be honest about the rush you get from this secret. It's clearly addictive, potentially destructive and the kind of thing most people look back on with regret. Why not stop while you're ahead?

At 18, this girl is of legal age to use the app. But as a high school senior, she might be hooking up with you for reasons you're not prepared to admit. Most 18-year-olds would think you're old and therefore gross, far too gross to hook up with.

You must have considered this. If she's not acting out in rebellion against her parents or culture, she might be exhibiting early signs of a mental health condition. If not, then she's one of the extremely rare 18-year-old high school students who mature early, have no patience for the immature antics of peers and feels ready to explore her sexuality. However, 18-year-old girls who fall into that category aren't sneaking around. Although their parents may not like it, these teens are very direct and honest about who they are and what they're doing. They're usually also in therapy.

The fact that you're hiding this relationship is significant. At some level, you know you should not be hooking up with an 18-year-old but refuse to stop yourself. The shame creeping along the edges of your conscience will flood it soon, if it hasn't happened already. When it does, expect your life to implode.

Don't want to look back with 20/20 hindsight, kicking yourself for hooking up with a coworker's kid sister, a connection you feel compelled to hide? End it now. For your sake, and hers.

I’m single and it sucks. Everyone worth being with got married in their 20s. Dating apps are a joke. Why is dating so broken?

Dating has always been challenging. In prior generations, people primarily heard about love, sex and heartbreak from a close-knit circle of friends. Their perspective was limited. Now with more ways to connect, we're inundated with everyone's struggles. Gender dynamics are also in flux. While that's a good thing, it sparks confusion: Who should initiate the date? Pay the bill? Is being exclusive still cool?

Another issue: People don't speak up about what they want or where their boundaries are. They think attraction is magic and a true love would already know how to please them. It's crazy, but rather than diss dating, think of it as an activity to practice, like snowboarding or public speaking. Have fun, get to know yourself and build your love expertise.