The Online Dating Game: Rules and Tips for Looking for Love

Looking for love—or even like—in the digital age has its own special set of rules.


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When the Marriage Doesn't Work Out

online dating

Illustration by Brooke Hagel

Illustration by Brooke Hagel

*Writer's name has been changed.

When I got married, I figured it would be for life. That’s how it worked for my parents, so surely it’d be the same for me. But 14 years of marriage and two teenage boys later, it didn’t quite play out that way. I found myself a working 40-something exploring the intimidating—yet admittedly intriguing—world of online dating. Considering I don’t buy my clothes online, I’m not sure why I assumed I could find the “right size” man on the internet. Still, I ventured out, learned valuable lessons and felt compelled to share with anyone in a similar situation. Learn from my mistakes—and remember to have fun.

Soccer Mom, 40s

Divorced career woman with kids who is finally ready to get out there and meet the real McCoy. Seeking an honest guy (with himself and with me), confident but not cocky (and knows the difference). You should like what you do for a living, know how to communicate and must have a great sense of humor. Please truly be single and definitely don't call me baby, send pics of your manhood or do drugs of any kind. All I’m looking to find is a smart, fun, driven, caring guy who likes to laugh, travel, movies and doesn't mind my crazy schedule. Am OK with FWB but not looking for LDR or MBA. [Not sure what these mean? See translations below.] Let’s talk first and then go on a date...remember those?

Tip #1: Don't be afraid!

First I had to realize/accept that online dating is an “in” thing. It’s no longer considered weird or creepy. In fact, it’s now just another part of our dating culture. Case in point: I was in a boutique with my boys and I snorted out loud when I noticed this label: “Soap for ONLINE DATING…Smells like a 10-year-old picture of someone else entirely!” Speaking of smell, online dating is very different from meeting someone in person for the first time , where you can see how they look and act in a public setting. And even how they, yes, smell. I had two incredible dates with a man who online seemed like an ideal match. When we met up in real life our chemistry was awesome, except for one thing…he smelled like an old man. (BTW, it’s an actual thing, the old person smell—it’s a chemical we produce as we age called nonenal.) He was in his 50s, intelligent, in great shape—ran half marathons every six months—traveled the world. So obviously not an old man. But damn, he smelled like one and I just couldn’t get past it!

Tip #2: Don't assume online pictures are recent or even close to reality.

You can hope and pray that people are posting real-time photos, but sadly, that’s not always the case. One guy’s profile stated he was 6 feet tall. He looked pretty buff in his pics, wore hats but bragged about his “silky brown hair.” I arrived at the sushi place and he was not only much shorter than stated, but bald. Now, I’m OK with bald guys. I even went through a bald-dating phase, but it caught me off-guard. I mean, he didn’t just omit something—like his hair or lack of it—he lied. That’s kind of a deal breaker. Not that lying is specific to one gender. My male friends have had their share of misleading encounters too. It makes me sad and angry for those of us who are trying. I hold steadfast to my pics being recent (within six months) because seriously, the guy is going to find out I’m not as skinny as I used to be (did I mention those two kids?) or my hair was once longer, so why not be genuine and show him the real me? After all, don’t I want to see the real him? In fact, I now automatically flat-out ask if pics are recent. If he gets defensive, I assume they probably aren’t. And I am done.


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Get Started the Right Way

online dating

Illustration by Brooke Hagel

Illustration by Brooke Hagel

Tip #3: Speak on the phone.

It may sound archaic, but I never meet a guy unless we’ve spoken first. No matter how much you think you “know” them after chatting online (or admittedly even on the phone), remind yourself that they’re still a stranger. I always call for the first time from an unlisted phone so they don’t have my cell phone number. (Being a single mom, I keep my home phone number unlisted as my work phone wouldn’t be hard to figure out.) Right away you’ll know if their voice irritates the crap out of you (a great guy I was really excited to meet struggled with putting a sentence together and sounded like a meathead) or they may not be able to carry a conversation. Thanks to the mobile world, so many people have forgotten how to just talk to each other. (Dear Lord, I sound like my dad. Forgive me, but he’s right!)

Tip #4: Be honest from the start.

Remember the bald guy I met for sushi? We sat down and after chatting a bit, he says he can’t hear me and asks to sit closer. Hesitating, I agreed. He ordered a glass of white zinfandel…for himself. I quickly ordered a dirty martini. Double. He starts telling me about his first wife and their troubles. “First?” I asked. Turns out he was married three times—and amazingly, all his wives had bizarre illnesses that ruined their relationship. Somewhere during this conversation (with me texting my girlfriend to please save me), he grunted. Not a clearing your throat grunt, but a noise so loud it attracted attention from other tables. He didn’t seem to notice or be embarrassed and kept talking. Again, the loud grunt. He continued talking. I ordered another martini, then silently begged my friend to call. While he was talking about how he wanted to take me away for a romantic weekend and all the things he’d like to do with me, there were at least three or four more loud grunts. I giggled. He didn’t seem to notice. I excused myself to answer my long-awaited call, still giggling. When I returned to the table, I told him I had a work crisis. As he reached for my hand, I gently pulled it away and explained in the nicest way possible that I just didn’t feel any chemistry between us and hoped he’d appreciate my candor. Fuming, he threw money down on the table and rose to leave. I walked out with him, apologizing again (for some unknown reason). “That’s a nice car,” I noted as we passed a beautiful convertible. “Yup, it’s what you would have been going home in had you not blown it.” Wow. 

Tip #5: Meet in a public place and have an exit plan.

The sushi restaurant was my choice. I chose a public place and told two friends where I’d be and when—a HUGE tip, ladies. Never meet a stranger (cannot overemphasize how important it is to remember he’s a stranger, no matter how many hours you’ve “spoken” online) without anyone knowing where you’re going. Apparently, aggressive or uncomfortable behavior is common with online dates. When I was in a bar recently with a friend, I noticed a sign in the restroom that read: “Are you on a date that isn’t going well? Is your Tinder or PlentyOfFish date not who they said they were on their profile? Do you feel unsafe or even just a bit weird? We’re here to help. Just go to the bar and order an Angel Shot. Neat: Your bartender will escort you to your vehicle. With Ice: Your bartender will call an Uber or Lyft for you. With a Lime: Your bartender will call the police. We’ll handle things discreetly and without a lot of fuss.” 

First off, how awesome is that? Second, how sad is it that it’s such a common occurrence they need to offer help in the first place?! That’s why I have to reiterate: Daters might not always have the best intentions. And you don’t need to depend on a sign to have an escape plan. Formulate one yourself. And work out a system with a buddy. For example, if you text _____, this means “Order me an Uber.” If you text ____, it means “Call and save me” or “Come pick me up immediately.”


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Have a Plan

online dating

Illustration by Brooke Hagel

Illustration by Brooke Hagel

Tip #6: Online dating requires strategizing.

Now, to those men who didn’t have recent photos, I could give some the benefit of the doubt because it truly is a full-time job to keep your profile and photos updated on all the sites. This is probably what surprised me most about the process: How much work is involved! Here I wanted to try online dating to make my dating life easier. And yet, often I find myself thinking it might be easier to smile and flirt with a man in a bar instead of going through all the work of setting up an account—writing an appealing, yet realistic, profile; finding photos that are flattering yet appear genuine (do you show full body or just head shots? With friends or solo? With dog or without? Show your kids?); tracking who has looked at your profile and researching theirs; responding to those who reach out to you that you may be interested in; declining those who you have no interest in; reaching out to prospects you might be interested in; and keeping up with everyday real life too. It’s more effort than managing Facebook, Instagram, Snapchat and Twitter combined. Andthis is all prior to going on an actual date!

Tip #7: Know your goal.

Want to get back into dating? Make some new friends? Establish an exclusive relationship? Find your soul mate? Remarry? Knowing—and being honest about—your intentions will help you meet others online with similar expectations. I recently completely clicked with a guy. After a couple awesome dates, he shared that he can’t get attached because he was moving back to Boston. This would have been nice to know when we had first met. I’ve also had some horrible dates, like the guy who fell asleep at the bar table while we were talking. (He was stoned. Who knew?!) And then there was the guy who asked for a favor related to my workplace during our first and only date.

Of course, there are plenty of good guys out there. I’m friends with several of them. What’s key is just getting out there and being honest with them, and with yourself. That’s the hard part. Not every site is for every woman. But you won’t know until you try. 

Bonus: Know the lingo.

WLTM Would Like To Meet

PF/PM Professional Female/Male

d Divorced

mba Married But Available

mnc Married No Children

ns No Smoking 

ld Light Drinker

420 Recreational Drugs 

si Similar Interests 

wtr Willing To Relocate 

fwb Friend With Benefits

STR Short Term Relationship

LDR Long Distance Relationship

MW4W Man And Woman For Woman

GSOH Good Sense Of Humor

TYVM Thank You Very Much


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Safety Tips and Other Dating Reminders

online dating

Illustration by Brooke Hagel

Illustration by Brooke Hagel

Call and ask the bar if it has a guardian Angel Shot on its menu before you head out for a drink date. How you order it lets the bartender know what to do next: 

  • Neat: Be escorted to your car.
  • With Ice: Call you an Uber or Lyft. 
  • With a Lime: Contact the police. 

Remember: If it doesn’t feel right, it probably isn’t. How a person reaches out/responds to you reveals a lot about their personality. If a guy merely sends me “hey,” I don’t bother responding. That may not matter to you, but it does matter to me.

Be yourself.
Not your best self or the self you want to be—be the real you. Save yourself (and the other person) the time and trouble of playing games.

Make your profile as multidimensional as you are.
Yes, you have a good side, but interested people want to know who you are, not just what you look like. 

Don’t trust a picture.
Go for personality revealed during an email chat or call.

Have coffee or non-alcoholic drinks the first time you get together.
I admit, this tip is from friends. Personally, I like a glass of wine to help me relax, but a non-alcoholic-drink date keeps it quick and honest.