Dating Advice: How to Flirt Your Way to a Maybe Definitely

I may not be married (coughyetcoughBRIAN*), but I like to think that I was really good sometimes, sort of okay at dating. Which makes me an excellent advice giver. Honestly, though, I’m much better at giving advice than taking it.


See? Even Katie thinks I’m very wise. Sage-like even.


I’d been dating a few different guys for a couple of months. One would flake, and I’d start dating another. I was seeing two to three at a time, always talking to someone new so I didn’t totally obsess about any one guy at any one time (this plan, by the way, worked in theory only. I was still bat-shit crazy). Online dating was my escape from the not-what-I-planned life I was leading.

I was a server in a bar with damn near a master’s degree, not really sure which direction I wanted to go in. But boys were always there to occupy my mind so I didn’t have to think, let alone worry, about my future. It was freeing and constricting all at once. I was just having fun, until I wasn’t and then I’d move on to someone new (okay fine, they’d move on to someone new, so I would have to as well). And then sometimes, I would go on the WORST dates with awkward guys who had nothing interesting to say or that I had no chemistry with. And quite honestly, when you get an unrequested, uncalled for, unnecessary dick pic (not to be confused with a Nic pic) from someone you’re already not interested in? Gah. I don’t miss that.

During this time, a couple of guys asked me to go to Europe with them. And then I  digitally stalked one of them. And got a little bit crazy. But somehow managed to see them again at the bar.

I didn’t hear from either of them after they failed to meet me at my preferred local watering hole. I was a little more than disappointed.

But with all my experience, I  had discovered the online secrets to making boys want to date me (at least go on a first date with me…or send me photos of their prize possessions).  With these brilliant pointers, you’ll be on the road to love in no time.

How to Awkwardly Flirt Your Way to a Maybe

Dating Advice

Leave adorable messages with near strangers

So when The Grown Up showed up in my Gchat feed a few weeks later, after one of those aforementioned really awful dates…I messaged him.

9:15 AM…
Me: So, I haven’t seen you guys around the (insert abbrev for the bar I worked at before abbrevs were cool) lately…Hope things are fabulous 😀

Be patient

44 minutes later…
TGU: Everything’s been going great! Bright and Shiny started his tax season rush, so he’s pretty much under house arrest until April. How’ve you been? You’re probably settled in at the bar by now.

Demonstrate positivity, ambition, and confidence

Me: I’ve been pretty great.
Settled, yeah…but I’m ready to get a teaching gig, so now its all about the hunt 😀
TGU: well…traditionally…you want to either isolate the young or the old and infirm from the rest of the pack. You can do this through several feints designed to see who lags behind.

Laugh at his jokes

Me: lmao
Good plan
TGU: or you can set a trap.
Traps are kinda more fun because they have an arts and crafts thing going on.
You can do a snare, a pit trap with spikes, a bear trap, a tripwire with claymores, a landmine…
Endless fun!
Most teachers will never see it coming
Me: hahahahahaha
I’ll keep those in mind…

Leave him wanting more

Me: Well, I wish I could chat more, but I have to run…breakfast calls me…

Ask him out without asking him out

Me: we should hang out or something sometime :-p
TGU: Definitely. but I’ll know to look for traps now.
I’ll check my schedule and shoot you an email.

Feign indifference

(but feel free to dance around like a maniac because you’re in your bedroom chatting and not next to him)

Me: Awesome. Sounds good
Later 🙂

Let him have the last word

TGU: Have a good breakfast

Obviously, I charmed him with my amusement and very serious flirting skills. He said “DEFINITELY.” That was good, right? I was ready to make this a thing. It had been 3 months since my first interaction with this very handsome man, who appeared to be mildly interested in me. I found myself screaming in my head, WHY WASN’T ANYTHING HAPPENING YET!?

How do/did you flirt with someone new? Were you an advocate of the digital dating or did you prefer old-fashioned, classic dating?

Did I go on a date with The Grown Up or was he all talk and little action? Maybe. Definitely. Click the image below to read the next part of the story!

The Waiting is the Hardest Part

Hey! Did you know you can buy my book on Amazon? 37 women wrote about the struggle for perfection, and I'm one of 'em. Go check it out!

That One Time I Had a Concave Nipple and Why I Hate Being Knocked Out

Warning: Contains a story about serious pain (and boobs). If you get squeamish when reading about pain (or boobs), this is not recommended.

Photo by Viktor Hanacek

Photo by Viktor Hanacek

When you’re 18, and you’ve ignored a giant growth in your boob for a few years longer than you probably should have (especially when the cancer runs in your family), you think it’s probably a good idea to ignore it for a few more years.

At this point, I’m going to go ahead and remind you to (and I quote), “DON’T DO WHAT I DO!”

At the age of 21, I finally went to the doctor about a lump…it was big and it hurt. Dr. Google wasn’t really Dr. Google back then, but I was pretty sure I didn’t have cancer. I sat in the doctor’s office and she recommended that I get an ultrasound.  The ultrasound, in which I laid on a table with my tit out in the open for yet another stranger to see, showed a gigantic tumor that was probably benign, but they didn’t know for sure. It was then I was told to visit a surgeon who handled that sort of thing. If it was painful, and oh my God it was, we were better safe than sorry in removing it.

So I made my way to the surgeon for a consult. My mom was in the room with me, and the surgeon asked all sorts of questions. There’s something uniquely awkward about sitting topless on a cold metal table in an exam room with your mom, a probing doctor and perky nipples, but there we all were. The surgeon explained that he was going to do a biopsy (I wasn’t sure what that meant), but he was going to numb it with an anesthetic first and OH MY GOD HE JUST WENT IN FOR THE FUCKING KILL.

I screamed bloody murder with pain as this alleged medical professional stuck me right under my nipple with a needle the size of a ruler and NO warning whatsoever. As tears ran down my cheeks, my mom looked on a little horrified at my reaction more than the doctor’s action. I wanted to yell at him. I wanted to punch him. I wanted him to stop whatever he was doing and die seventeen painful deaths.

I hated him.

Apparently, (and this is according to my mother, because I completely blocked out the rest of this memory), like 5 more needles made their way into that wickedly painful-without-needles mass under my left nipple.

I left the consult with plans for surgery. And no idea what to expect.

When I had my surgery, Mom came with me (my boyfriend at the time wasn’t really the most supportive boyfriend) and waited the whole time. I remember getting prepped for surgery and being rolled into the OR. One of the 15 medical professionals in the room told me that they were going to give me an anesthetic that was going to knock me out. Of course, I couldn’t resist asking them what would happen if I woke up mid-surgery? Or what if it didn’t put me out? And could I keep the tumor? They assured me it would be fine and the mass was not for keeping, so I cracked one last one-liner before they put the gas mask over my face and knocked me out for however many hours.

When I woke up, I was in a hallway. There were people all around me; I was shaking, freezing, and…I couldn’t move my body. My eyes popped open, terrified. I kept shaking, but I couldn’t move my arms. Or my legs. Or my head. Or (ohmygodpleaseletitnotbeso) my MOUTH. I couldn’t speak. I could hear everyone around me, talking, ignoring me. FINALLY, they noticed the shaking, panic-eyed girl on a gurney. “She must be cold.” Duh. So, they put this magic plastic blanket over me that had a large tube pumping hot air through it. I wanted to live under that blanket forever. I was almost okay with not being able to talk. Or move. Because that blanket was the heaven that I was waiting for after my body died stopped working.

Eventually, I regained the ability to speak (obviously). And to move (maybe not quite so obviously…or gracefully). And I vowed never to go through THAT again.

Once I got home, took a looooong nap, and was finally ready to rejoin the living, breathing, working world, I took a peek at my recently-sliced knockers.

What. The. Ever-living. Fuck?

There were serious stitches. And. What the hell happened to my left tit?

Apparently, the large jalapeno-sized tumor that was removed from my boob had left a ridiculous gaping hole in the middle of my breast tissue, thus inverting my nipple in the craziest way.

After I came to terms with my newly shaped booby, I decided that it was my job to share it with the world. Or at least my best girlfriends. I was a junior in college, living with 3 other girls in an apartment…I showed them and any other lady friends that were around. I’d get drunk and say, “Dude! Wanna see my concave nipple?!” And of course, the oddity that was my boob was kind of a party trick for several months. (My boyfriend at the time would not have been pleased if I was showing my boobs to dudes, so it was just lady friends). After almost a year, I figured it would never be a normal boob again.

Low and behold, over time, my boob went back to normal and I wished I had taken pictures of the concave/inverted nipple that amused the shit out of me for so very long. And I was okay with that.

What I learned from this experience: Go to the doctor even if you’re scared. You may find out that you’re allergic to vicodin, and that you hate anesthesia, and that the surgery changed your body for a freak-show party trick…but the initial problem will be gone. And you’ll live to show off your party trick.

Have you ever had a surgery render your body a little bit different than it used to be? Have you ever been under anesthesia? Do you hate doctors who inflict pain on you? Did you ever wait to do something because you were scared of the results?

Hey! Did you know you can buy my book on Amazon? 37 women wrote about the struggle for perfection, and I'm one of 'em. Go check it out!

Meanwhile, a Little Awkwardness in the Ladies’ Room…

Holy crap, you guys. Brian and I are safely in California, checked into hotel number one of three for the first leg of our trip, and I already have 27 thousand things to tell you.

The Pros and Cons of Midol

I pack VERY light when it comes to my carry-on luggage, if I can help it. Not so much with the checked luggage, though…I check everything, thanks to Southwest’s Bags Fly Free policy.


Yes, my suitcases are that big...and that girly.

So when I realized my sinus infection headache was not going away after Allegra, Sudafed, and an antibiotic, I also realized I had packed the Advil in my suitcase. I ran to the shop for a quick headache relief solution, only to be appalled by the gouging prices of everything…except Midol.

I hadn’t used Midol since college, before I started the pill to help dull the effects of my period. But a dude-friend of mine swore by it in college, for obviously non-feminine reasons.

I swear to God, you guys, it was a magic little half-priced pill. I started feeling it break up my headache within minutes. Within an hour, it was gone.

Of course, three hours into our flight, I had to pee…in the teeny tiny bathroom. Insert expletives about the size of my hips here.

I can’t claim that this is 100% correlation so much as coincidence, but I’m telling you…Midol brought my monthly curse right there on the plane. And also a weird dream about my lady eggs. Fucking Midol.

My Whoops Moment in the Airport Bathroom

After our hour plus delay at Midway Airport in Chicago, we arrived safely at SFO. Having only used that sorry excuse for a bathroom on the plane once in a 4 hour trip, I had to pee immediately.

I went into the ladies’ room where there was a crowd of women and just one older woman with a little guy in front of me. She was checking a door to see if someone was in there, but it didn’t open, so she told the little boy, “Nope. Someone is in there.” I noticed that the first stall was empty by peering into the little door hole, and instead of taking it for myself, I pulled it wide open for the little boy and his mom or grandma (not sure which), while I stood behind the door, proudly being helpful. She looked at me, horrified. “Nope. Someone is in there.”

I slowly closed the door, and looked around, nervously. A sweet teenage girl tried to reassure me that it was probably no big deal, but I considered running out of the bathroom faster than I had ever run in my entire life. But thrn my overwhelming urge to pee won, and I stared at every stall waiting for one to open.

The toilet flushed in the stall I had opened. It was now a race between 7 other stalls and this lady. I just needed one to open so I could quickly duck inside. Her stall was about to open, when another miraculously became available. I dashed in, just as the woman was about to walk out. I saw a flash of color from her skirt before I was safely in my own stall.

When I walked out to wash my hands, I’m pretty sure she was still there, taller and scarier than I hoped…she could totally beat the crap out of me…but I walked (or slinked…one of those) to the sink next to her with my head down, avoiding all eye contact with anyone. I washed my hands and raced out of there, paper towels still in hand. I gave Brian the look that says OMG let’s go go go.

“Awkwardness in the bathroom?”
“OK then.”

And we moved on to baggage claim.

What are your thoughts on Midol? Have you ever accidentally opened a bathroom stall? Have you been walked in on?

Hey! Did you know you can buy my book on Amazon? 37 women wrote about the struggle for perfection, and I'm one of 'em. Go check it out!

That One Time You Asked Me For Ridiculous and Impossible Blog-Souvenirs From My Vacation? This is What You Get.

I was on vacation. For a whole week. 8 days to be exact. 8 days out of Chicago. 8 days out of the cold. 8 days in Florida. On a tiny little island, where grandparents hang out with each other and walk on the beach together with Chrissy. You asked me for the following:

  • Gators modeling swimsuits.
  • The hottest guy you can find. I want the six-pack, tattoos and everything. And you can say it was totally my fault if you get in trouble. SEE, I’m already a bad old lady!
  • Every beach has “that guy.” You’ll know him when you see him. I want to see him and maybe a great woman in a two piece suit to remind my wife how fun vacation is and that we need to start saving if we plan on going.
  • Awkward people.
  • Maybe a great pic of you and Brian and a palm tree.
  • Dolphins!!
  • Toes in the sand (a request from a Google Hangout)

Unfortunately…I didn’t see ANY gators in swimsuits. The lucky bitches were all naked.

Turtle gator ride

Would you settle for a turtle taking a gator ride?

Finding hot guys on Marco Island is tough. I totally was a creeper and took this one, just for you. Closest I could find.

The back end of a hot guy

The back end of a [maybe] hot guy (also includes “that guy” and one of the “awkward people.”) Fuck, I’m awesome.

OK, fine. You asked for awkward people. As if that guy isn’t enough. And me taking a picture of those two guys. And really, me in general…I’m pretty fucking awkward. But fine.

And if that’s not enough for you, I went all the way. I randomly video’ed the beach just to show you how far I’m willing to go for you guys. Point out the awkward, hot, etc etc…BTW, the guy reading the book? Totally hot just because he was reading a book. That is all.

My mom wanted Brian and I by a palm tree…

Beach vacation

There are palm trees back there somewhere

I fucked up on the dolphin picture. So I didn’t really know how to work my camera on Day 1…when the fucking dolphins were 20-30 feet off the shore. Brian’s dad kept telling me to run in to swim with them (not understanding that I wanted to PAY money to swim with tame dolphins…not get raped by wild dolphins…)

So here are dolphins from last year.

Dolphin pictures

OK fine. This dolphin is from 2 years ago. You love me anyway, right?

You really don’t WANT to see the Flintstoes…but I’ll show ’em off anyways.

Things you didn’t ask to see, but I’ll show you for funsies:

So, Blog Friends, I’ve got a few more posts with random happenings from last week lined up, but based on the pictures above, what do YOU think happened on my vacation? Tell me a story. The funniest story wins a fabulous mystery prize. Ready. Set. Go.

Hey! Did you know you can buy my book on Amazon? 37 women wrote about the struggle for perfection, and I'm one of 'em. Go check it out!