How to Survive Prom Night Without Regrets

I didn’t actually go to my own prom.

By the time it rolled around, I had already been to a few others as someone’s date—and those experiences left me so disillusioned that I skipped my own and spent the night in the woods with a couple of close friends instead.

Let me explain.

Once, I was asked to prom by a friend of a girl I was dating. I was pretty naïve going in, but it quickly became clear that she had more than just dancing on her mind. After the dance, we took a limo to the beach—which was pretty standard where I grew up in Long Island in the early ’90s. My date got drunk and started acting more and more aggressive—trying to make out with me, despite being a friend of my actual girlfriend. I wasn’t expecting that at all.

Eventually, she got so pushy that she literally knocked me off a pier. I fell about ten feet to the parking lot below, tearing my tux and scraping up my left butt cheek. Not exactly the night I had imagined.

Looking back, I realize something important: I had never even thought about what my boundaries were. I didn’t have a plan—and it showed.

There’s an old saying: “If you fail to plan, you plan to fail.” Here’s what I wish I’d known back then. Let me give you three things you can do to protect your sexual integrity and still have an amazing time.

1. Set Boundaries

When I was your age, I didn’t understand the importance of limits. My mother put condoms in my Christmas stocking as a freshman, so I assumed everyone simply did what felt right in the moment. No one suggested there might be a better approach—until experience taught me otherwise. I hadn’t considered where to draw the line, and it cost me. A night that started with promise ended in a torn tuxedo and a painful fall. You can avoid that kind of trouble by deciding ahead of time what you’re comfortable with, because without a plan, it’s easy to lose control. 

What does “too far” mean? It varies for everyone, but here’s a practical measure: if it involves undressing, touching private areas, or anything beyond a brief kiss (saliva aside), you’re likely past a manageable point. Affection isn’t the issue—holding hands, dancing, or sharing a respectful goodnight kiss doesn’t cross any lines. But if things escalate to intense kissing or more, restraint becomes difficult. Momentum builds quickly, and it’s hard to step back once it does.

2. Manage Expectations

Once you’ve set your boundaries, it’s essential to share them with your date. Prom carries a lot of emotion and unspoken assumptions. If one of you expects a romantic encounter and the other doesn’t, the evening can become awkward—or worse. Misunderstandings like these can derail the night. Discuss it beforehand. It doesn’t need to be a heavy or uncomfortable exchange. You might say something like, “I’d prefer to keep things simple—holding hands, dancing, and perhaps a kiss goodnight if it feels right. I hope that works for you.” Or you could frame it differently:

 “I’m looking forward to a relaxed night. I’d like to stick to holding hands and dancing, with maybe a goodnight kiss if we’re both comfortable with it.” 

When you’re both on the same page, the pressure fades. You can enjoy the evening without guesswork or tension.

3. Have the Time of Your Life

For most people, prom only happens once (or maybe twice). So dance. Laugh. Make memories. Take too many pictures. Celebrate the people around you and the milestone you’re hitting.

And now that you’ve set your boundaries—and clearly communicated them—you’re free to actually enjoy the night without fear, guilt, or confusion. You don’t have to wonder if you’re compromising your values. You can walk away with zero regrets.

One Last Thing: What If I’ve Already Messed Up?

For most people, prom is a rare occasion—once, maybe twice in a lifetime. It’s a chance to dance, laugh, and create memories, to take countless photos and mark the moment with the people around you. Once you’ve established your boundaries and shared them with your date, you can embrace the night fully. There’s no need to worry about overstepping or second-guessing yourself. You’ve set the stage to leave with no regrets, confident that the evening reflects what matters to you.