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Why You Should Meet that Online Crush in Person Sooner Rather than Later

I was supposed to be working on my writing exercise. After telling myself I was going to attend a local writers Meetup for over a year I finally dragged myself out into the world and did it. I was at a neighborhood coffee shop, surrounded by eight other women writers from Seattle, and we were doing a 10 minute character exercise. Except I couldn’t concentrate.

I couldn’t concentrate because there was a first date at the table next to me. And they’d clearly met online. And it was clearly uncomfortable for both of them.

To be perfectly honest, I could sit and listen to first dates all day long if I could. I love those first moments of sheer terror, of hope, of uncertainty, of wonder and fear.

One of my first serious, head-over-heels crushes was with a man I met online. Or, we were introduced online by a mutual friend and started exchanging emails. And lemme tell you, hot shit was he dreamy and witty and perfect.  And for the first time in my life I felt genuinely desired by a man, which made me feel more drunk than if I’d been on a cruise with free booze.

He lived in another state. And about two months after we talked exchanging emails (and talking on the phone) he visited with a few mutual friends and we quickly brought out some board games. It was a competitive game, one that required teams and guessing and drawing.

What I quickly realized, with my stomach dropping and my cheeks lightly burning, was that he was not the easy-going, carefree person he’d seemed over email. In fact, he was sort of nasty. His idea of a joke was a cruel stab at his friends intelligence and a mocking comment on another’s slow response. He grew defensive when he got an answer wrong. He argued about the timer, the drawings, the score.

The charming and lighthearted man I’d fallen for over email wasn’t exactly charming in real life. And I found myself wishing we’d met in person much, much earlier. I wish I’d seen the way he rolled his eyes at people. I wish I’d heard his tone of condescension. I wish I’d felt the way he repeatedly told me to “take a joke” as if we were in third grade and the gum I’d just sat in had been my fault.

It was such a bummer of a night.

But you know what? I’m guessing I was also a different person than I’d portrayed online. I’m sure I wasn’t as confident in person, as sassy, seductive and easy-going. I imagine he was expecting someone else, too.

But this is also why I tend to encourage people who are connecting online to meet in person sooner rather than later. While my anxiety and ever-growing-tendency-to-stutter makes me appreciate the chance to clearly communicate my thoughts and feelings via writing, I also know how impossible it is to reflect those subtle personality quirks online. They can’t see the way your smile blooms when you see a dog walk past the coffee shop window. They won’t see the way you gently thank the barista as they hand you your drink. And these moments are what make us truly fall for each other.

Let’s just get the cliche out in the open: actions speak louder than words. That shit’s the truth.

It is exhaustingly scary to plan to meet up in person. But it will also allow you to quickly realize whether or not this is something you want to pursue or if there might be a better fit for you out in the world. Because let’s be honest, anyone who threatens to throw a Taboo buzzer across the room because they got an answer wrong is not sexy.


You’re Not Alone if You Feel Nervous About Dating

Something really cool has happened over the past few years. I started this blog in 2013. It began as a place where I could think through pain points I’d had while trying to date as I also dealt with anxiety. One of my mantras when I thought about starting this blog was, “I can’t be the only one.” As you guys have shown me, I’m not.

And I have the evidence to prove it.

This site is powered via WordPress. There are thousands of people who find my blog via search engines online (Google, Bing, Yahoo, etc).

For 95% of these searches I’m unable to see the words people typed in that led them to this site. But for the other 5% I can see what someone searched for. There are no other identifying factors for the search terms, so there’s no way to know the person’s age, gender, hometown, etc. Yet this anonymity makes me feel all the more connected.  And it’s one of the coolest things.

In 2016 so far here’s a sampling of what people are searching for on the internet.

One thing is for sure; you are not alone.

I love you guys.

Sampling of 2016 Search Terms

dating anxiety

how to date when you have anxiety

anxiety while dating

late bloomer in dating

anxiety after first date

overanalyzing after date

holding hands gives me anxiety

nervous after first date

if a girl asks you to grab coffee

first kiss in 30s

i panicked after a first date

new relationship anxiety

feeling nervous after first date

anxious after a really good first date

nervous about first kiss

being a late bloomer in dating

what should i talk about on first date

how to not be anxious over the phone

things to talk about on a date

so nervous about coffee date

(and my all-time absolute favorite one..)

blind date diarrhea

I Hung Out With a Friend While He Tried to Work Up Courage to Tell a Girl She Was Pretty and MAN It Was Stressful

We hovered around him like buzzards surrounding a fresh carcass.

“Just get in and get out,” Friend 1 shouted at him.

“It’ll be over so fast!” Friend 2 added.

“Come on, don’t chicken out,” Friend 3 contributed.

“If you don’t do this then you’re dead to me!” Friend 4 screamed, spittle flying from their mouth and also I should mention Friend 4 was me.

We were out at a bar for our friend’s 24th birthday. The rest of the group, myself included, had a mean age that fell in the 30 – 35 age bracket. However, we’d all met and bonded at the same dark, cramped bar here in Seattle, all rooting for the same English soccer team. They are friendships formed over shared hatreds of opposing teams and shared beers at 6am kickoffs.

Our spring chicken of a friend, the one now turning 24, will sometimes talk about crushes with us at the bar, girls he might find cute or intriguing. We tend to grill him, digging furiously through his hesitant collection of information, foraging for clues of scandal or intrigue. Ever the gentleman, he rarely gives us much to gnaw on.

But then we went out for his birthday. At a bar we don’t usually frequent, one located directly across from a University downtown, and one that transforms into a college party at the stroke of 10pm like some perfectly contoured and styled Cinderella-building. We got there at 9 and within an hour I became acutely aware of how long it’s been since I hung out in a college bar. I was like some white lady Hannibal sitting there staring at the 20-something girls saying “look at her skin” under my breath.

Our birthday friend mentioned he thought a girl was pretty. He said he wished he could tell her. We pounced on him like he’d casually mentioned he had a million dollars stored in his coat pocket.

“Just do it casually,” Friend 1 said.

“Don’t overthink it,” Friend 2 said.

“Be yourself,” Friend 3 said.

“Do you think she uses a special moisturizer?” Friend 4 said.

We threw endless suggestions at him, tossing baseballs of empty cliches at his face as if it would help.

His face quickly dissolved into a weird combination of anxiety and determination and suddenly I FELT ANXIOUS FOR HIM. Stupid empathy.

For what seemed like hours (but was probably more like 20mins) we watched him stand up, take a few steps in her direction, then come back to our table. He’d stand, shuffle a bit, mumble a few words, then sit back down. Over and over again. It became painful.

“She’s on her phone,” he said.

“There’s a guy at her table, I can’t tell her she’s pretty while a guy is there.”

“Her beer is almost empty, she might be getting up soon.”

“She’s back on her phone.”

After his sixth or seventh attempt where he discovered another reason not to talk to her I grabbed my wallet and pulled out a dollar. Anyone who knows me or reads this blog knows I LOVE a good bribe and by bribe I just mean a small symbolic object you get if you take a new step or do something scary.

I told him he would get the dollar if he went through with it.

After the eighth and ninth attempts he stood at the table staring at the dollar bill. At one point he muttered, “I want that dollar.”

Finally, he stood and began walking towards her. One of our friends stood and walked a few paces behind him, sheep-dogging him if you will, not allowing him to turn around this time.

And, spoiler alert, he told her she was pretty. She said thank you. And he got the dollar.

Guys, this was stressful. For any of you reading who are out on the dating scene trying to work up the nerve to talk to someone you think is attractive I BOW DOWN TO YOU. The fear of rejection is real and true. The depth of vulnerability that’s required to even do something as “simple” as telling a woman she is pretty, is monumental. So go ahead, give yourself a damn dollar the next time you do something bold.

Our 24-year-old friend doesn’t talk about his crushes all that often. But now, if he does, I’m going to flap my buzzard wings, fly away and leave him alone. I’ll simply tell him, “you do you, boo boo.”




Collecting Those Relationship Blueprints

It would be so nice if in third grade we all sat down, opened our Relationship Textbooks, and started learning a set of skills. But, unfortunately, that shit doesn’t happen. In childhood we aren’t all taught the skills necessary to build solid, strong relationships. For the majority of us we learn how to “relationship” by what we see and observe in the relationships around us.

I know, personally, that my anxiety often rattles around in my brain with negative thoughts. My skull is a gumball machine, my negative thoughts are hideously moldy gumballs, and they love to try and accumulate.

Over the years I have spent way too much time thinking about all the things I “should” be doing better or that I “could” have done differently. I have spent a lot of time fixating on what “might” go wrong in the near future/distant future/hypothetical futures. And when it comes to my intimate relationships and the years I spent trying to enter into the dating world I spent a hell of a lot of time hating myself and my patterns.

It’s really, really easy to get stuck in a merry-go-round of feeling helpless and fucked-over by X, Y, or Z. It’s really, really easy to blame yourself. To blame your brain chemicals. To blame a person at work. To blame the institutions around you. To blame your parents. To blame your friends. etc etc on and on and on until the world starts to feel very dark and sad. But whenever I find myself slipping into these caves of muck I remind myself I have a choice in how I shape my life and I need to make a motherfuckin’ plan.

When I saw a headline on the internet that Drew Barrymore was separating from her husband I felt a stab of sadness. The sadness didn’t come from any kind of obsession over their relationship or an obsession with Drew Barrymore (though I am a big fan). The sadness was rooted in a quote I’d read. It was a quote that stuck with me. Barrymore was discussing why she fell in love with her husband. She’d said he was “someone who has this incredible blueprint of a family that I don’t have.”

That idea of a blueprint stuck with me. It appeals to my pragmatic side, my planner side, and my poetic side that loves a good metaphor. And it felt really beautiful since it was Barrymore gently acknowledging her childhood/family hadn’t provided her with the skills to build a healthy relationship, but that didn’t make her incapable of identifying one she admired and moving towards it.

A blueprint is a design or a plan that can be followed. It is a detailed plan of how to do something.

A blueprint is something you can take with you, refer back to, and rely upon when you are feeling a bit lost.

If you find yourself stuck in that merry-go-round of negativity, sadness or feeling hopeless, remember that you are capable of building yourself an exit strategy. You’re capable of building yourself a new ride entirely. And you don’t have to figure it out all on your own.

Start by looking outside and finding examples of what you do want. Find examples of people who you admire, list why you admire them, and think through how they achieve these qualities. What do you imagine they do on a daily basis? What small steps can you take to get closer to this lifestyle?

There’s a fine line between observing others and feeling inspired and observing others and feeling jealous/cynical. Remember, there is enough love and happiness and beauty for everyone. Look at those you admire, feel happy for them, and use them as a shining light of guidance.

I’ve come to realize for myself how important it is to look out in my world and collect blueprints of people I admire. This is especially true when it comes to my intimate relationships and my marriage. Like the Winchester Mystery House, my marriage is something I will forever be building, forever working on. I want to make sure I have some BADASS blueprints to help guide me.

All of us, always, are learning what it means to be alive. And even though we may not sit down in third grade with our pencil and relationship textbook, we can sure as hell look around us and go THAT’S what happiness looks like.




Interview with Comedian Samantha Ruddy

If you haven’t heard of Samantha Ruddy yet you will soon enough. She is one of the funniest women on Twitter. She writes for College Humor. And she recently opened for Tig Notaro. Aka all around badass. I first came across her when I was one of the hundreds/thousands of people to retweet/favorite this  gem:


To me, comedy writing and stand-up comedians are the pinnacle of confidence and intelligence. I am seriously in awe of stand-up comics. I wanted to ask Samantha about being a creative person, living fully, and finding confidence. Samantha was gracious enough to answer our questions and I’m still pinching myself and asking, as Samantha sometimes does, Me? Seriously?

First off, can you introduce yourself to our readers?

Hi! I’m Samantha Ruddy. 

What initially drew you to stand-up comedy?

I’ve always loved comedy. Cliche, but true. I work well with others, but I love just getting lost in my head and writing, which I think lends itself to stand-up since you’re working mostly alone.

Was there ever a moment where you wanted to flip the table and walk away from writing comedy?

Not really! I think I’ve had too many other jobs where I wanted to do that. I get writers block, but it’s more of a disappointing thing for me than rage-inducing. Usually.

So much of stand-up demands you to put yourself out there over and over again: how do you keep yourself going?

Well, to be honest, I don’t think I’m too far on the intimate side as far as comedians go. Sure, I’ll talk about private aspects of my life occasionally, but not to the extent of other comics. I’m primarily a joke writer. Some of the things in my act are total lies. I always joke that I’m not even gay. (I am) I just want to write funny jokes. If it also happens to be true and intimate, added bonus! Maybe that’ll change as I grow as a comic. I’m only three years in. 

Do you ever struggle with self-doubt? If so, what do you do to overcome it?

Sure. I am on my way to open for Tig Notaro in a 1000 person theater right now and all morning I’ve just been like “Me? Seriously?” I like listening to rap music. Cause they’re like “I’m the greatest!” and it sort of rubs off on me to the point where I can be like “I’m okay!”

You speak openly about being a member of the LGBTQ community — what advice would you give to someone who is navigating the coming out process?

I think just be honest with yourself as soon as you can and come out to everybody else when it feels safe. I have a wonderful family who I’m sure would’ve supported me in high school, but I didn’t realize I was gay until I was about to head off to college. I always wonder what high school would’ve been like if I had figured it out earlier. Anyway, way to make this about you, Samantha.

What advice would you give to a young person who is pursuing a creative, “non-traditional” path in life?

Have a strong support system of friends who are doing similar things, but also, ones who work at banks and as teachers and are just like normal people. I don’t live with comics and I really love it. You get so wrapped up in this world and it’s nice to come home to people who can give you a break from it.

Name three stand-ups we should be paying attention to.

Casey James Salengo

Luke Mones

Janelle James

Those three all have very unique voices and are different from each other,  so everyone is bound to like at least one of them. Also they’re hilarious.

Name three, creative, non-stand-up friends of yours we should be paying attention to.

Annie Licata and Julie Kosin are both young journalists who work for Rolling Stone and Harper’s Bazaar, respectively. Both are great writers.

Jeanette Wall manages bands and runs a label called Miscreant Records with one of my favorite bands, PWR BTTM, on it. I want to be her when I grow up.


Thank you again to Samantha for taking the time to be part of the blog! Can’t wait to see where she goes next.

Follow Samantha on Twitter HERE
Check out her Reddit page HERE