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Have you seen the new commercial for Red Flag perfume by Chanel? Well, it’s not actually a commercial. It’s Saturday Night Live’s take, promoted superbly by my favorite comedienne, Kristen Wiig.

The red flags in this faux-mercial are hilarious. That extra long pinky nail is outright disgusting! But when it comes to dating, red flags are something that shouldn’t be ignored. Even more so with the semi-new frontier of online dating, where it can be a bit more challenging to really get to know someone.

If you’re a regular reader of my blog, you know that I’m a big fan of online dating. It can be a great way to meet people, make new friends, and possibly even kindle a romance. But online dating can also open a Pandora’s box of crazy, and if you’re not careful, you could end up smack dab in the middle of a really bad situation.

Such is the story of Lily*, a fabulous and fun friend of mine. Lily is single, kind, beautiful and smart. And she’s a fearless dater—always up to meeting new people and trying new things. I actually wish I had a little of her courage in that department.

(*Name changed to protect her privacy.)

Recently, Lily met a guy on eHarmony named John**. They talked for a few weeks and she felt like there could be a connection, so they decided to meet up for a first date.

(**Name not changed because this guy’s a real douche bag.)

This first date ended up being a “first date weekend,” due to the fact that Lily accepted John’s proposal to fly her out to visit him. Lily lives near me in the D.C. area, and John lives in North Carolina.

Why, you ask, did John offer to fly her out, rather than simply flying to see her? Good question.

Red flaaaag.

Fearless Lily, who didn’t fill me in on this plan until after the date, boarded a flight to Raleigh. When she met John at the airport, she was greeted by a tall, burly man in cowboy boots and tight jeans driving a pickup truck.

John seemed nice enough at first. He told Lily he wanted to show her around his college campus (even though he’d graduated many years earlier). She obliged, though she wasn’t given much of a choice. The campus tour took about three hours… on foot. Detail after boring detail of every building, every sidewalk, every tree. All the while, John seemed completely oblivious to Lily’s boredom and fatigue.

Red flaaaag.

Exhausted, Lily climbed back into the pickup truck to head back to John’s town. He forgot to mention that he lived over two hours away from the airport… in the middle of nowhere. Literally, a house in a large field, with not one neighboring house in sight.

Red flaaaag.

Lily stayed in the guest room at John’s house—again, not a decision that was run by me before the date. (You should have seen the outrage on my face when I learned of this afterward!) By the time they arrived home, it was well past midnight and Lily was exhausted. Off to bed they went.

The next day, Lily woke to an invitation from John to attend a picnic. Every girl loves a creative guy! Sounds fun. Lily asked one simple question beforehand: “Who is going to be there?”

“Oh, you’ll see,” was his reply.

But Lily insisted. “No, I’d really like to know who is going to be there.”

“You’ll see when we get there.”

Red flaaag.

With flashes of possible appearances by in-laws and fraternity brothers running through her head, Lily reluctantly got into that pickup truck and they made their way to the picnic. As they pulled up to the busy park, Lily looked around at all the people, of which there were many.

She glanced at John. And he nonchalantly said,

“Did I tell you that I’m an elected official?”

Red flaaaag.

Before she knew it, Lily found herself in the middle of a Republican Party picnic filled with congressmen, mayors and John’s other colleagues. She was so annoyed that he’d take her to a public outing and purport that she was his girlfriend to complete strangers! It took everything in her to not yell, “I love Obama!” at the top of her lungs.

The rest of the day was a blur, and ended with them arriving back at John’s house for a little surprise. He’d planned to set up a wine tasting for her, right there in his kitchen. Sounds romantic, eh? He proceeded to take out various coffee mugs, and then opened the refrigerator to reveal several half-empty bottles of wine.

Red flaaaag.

He started pouring and Lily fought against her instinct to gag. Could this weekend get any worse?

They decided to play cards in the living room. Finally, she thought, some normal social activity.

As they were playing, he looked at her face. Not into her eyes… but at her face. She felt uncomfortable, because, you see, Lily had a pimple on her cheek. No big deal, really. Everyone gets zits. There was nothing she could do but dab a little cover-up on it and move on. But the way John was staring at it made her feel so self conscious.

Red flaaaag.

Then, suddenly, John got up from playing cards and went to the kitchen.

“What are you doing?” Lily asked.

He rifled through a junk drawer, making clanking and clinging noises as he apparently tried to find something.

“What are you doing?” Lily asked again.

He began to walk toward her holding a needle.

Red flaaaag.

And a lighter.

Red flaaaaaaag!

“What are you DOING?!” Lily finally yelled.

“Let me help you with the bump,” John said, in a creepy southern accent.


Lily jumped up, spoke her mind (You go, girl!), ran up to the guest room and locked the door.

It was 8:00 p.m. She stayed in there until morning.

The next day, Lily had to sit through a few more touristy things with John before he drove the two hours back to Raleigh for her flight home.

Needless to say, they never spoke again.

John is… well, let’s not sugarcoat this… he’s a loser. He didn’t have the guts to visit Lily where she lived for the first date, he dragged her around town all weekend like she was on a tour of Italy without so much as asking her what she wanted to do, he tricked her into being his date for a political event at which he was a featured guest, he served her old, stale wine, and he offered to pop her zit with a do-it-yourself sterilized needle.

But Lily could have avoided (or bettered) this situation had she been more careful to begin with.

Here are three things every girl should have in her pocketbook on a first date. I’ve shared these tips with Lily—a little too late, though hopefully they’ll help her next time around. And hopefully they can help you out, too.

  1. Home field advantage. Let him meet you where you are. Your town, your restaurants, your neighborhood (though not your residence). There will be plenty of time in the future for you to visit his neck of the woods. In the beginning, play it safe. Stay close to home.
  2. A limited agenda. Short dates are the best first dates. Plan a dinner, meet for lunch or even just grab a cup of coffee. It offers just a couple hours for you to talk and see if there’s that initial spark. And it’s easy to just say goodbye afterward—eliminating any feeling of being trapped.
  3. An escape vehicle. Drive yourself, take a train, ride the bus or hail a cab. There should really be no reason for you to get into a moving vehicle going 70 miles per hour with someone you don’t know from Adam. Apart from the obvious safety reasons, bringing your own transportation allows you the choice to leave. (A choice I’m sure Lily would have loved to make somewhere between the Tea Party and the pimple-popping brigade.)

Dating is a tough game. It’s not easy to get to know people, whether in person or online. But no matter how caught up we get in the fun (or pain) of it all, we need to remember that safety comes first.

When you see a red flag, don’t ignore it. And plan ahead, so you can avoid being in a potentially dangerous, awkward, embarrassing, gross, disgusting or just plain weird situation.