Category Archives: Dating

My Foray into Online Dating

Part One (it’s only been 2 weeks, and I’m sure there are more adventures to come after this posting)

Except for first dates (because those make me want to throw up), I in general like dating. Getting to know someone, talking a lot about yourself, and going to free dinners are all bonuses to dating. Since I’m new to Chicago, I decided that I needed to get myself out there in the dating world. I’m sick of meeting guys at the bar – I know, I know, I drink, too, so it’s not that strange to meet a “normal” guy at a bar, but every guy I’ve met at a bar has a commitment-phobia that I like to call “scared to sleep with only one person”.

So, in the spirit of trying new things, I recently went on a Grouper – it’s an online dating service where, based off of your Facebook profile, you’re set up on a date with someone. You bring friends, they bring friends, and it’s a group date (get it? grouper?). The average age of the guys was 23 and they still had peach fuzz on their chins; the average age of us girls was 30. You can guess where that ended up! Well, actually, you probably can’t… They paid for our drinks, then ditched us, not meeting us at the next bar that they asked us to go to. I’m sure they got a riotous laugh all the way to their mom and dad’s house.

A couple of girlfriends and I went to a singles’ mixer, and ended up meeting two cool girls who we spent the night eating dinner and laughing with over the quality of guys in attendance. Oh, and I also flirted it up with the bartender who was left my number on a coaster – and not by me. He texted, I didn’t meet up with him because I was nervous, ugh. I also considered speed dating, but freaked out and signed up too late, so instead ended up on a waiting list, got off said list, and didn’t try to get in. I was scared, what can I say?!

So…that leaves me with the very brave act of making myself a profile on OKCupid (and, no, you cannot find out my username). It’s actually been fun not responding to idiots who write things like:

*hello, you are such a beautiful woman….how come you are not taken? I spilled my cup of Coffee on my laptop just because I was taking a closer look on your pics…..lol….well i got it dried anyway.. How are you doing??? In a relationship what matters most is a true and honest man who will treat you right. I seek my soul mate, i am ready to treat you as my queen and princess, be your knight in shinning amor…My name is Denis Maillet, I am a very God fearing man and needs a woman as such that is why I contacted you no matter the distance between us, God will bring our heart desire to past. I am man who has dedicated his life in helping people who are in need and doing charity.Hope to hear from you

*Hello. Cupid called. He says to tell you that he needs my heart back. You have beautiful eyes:)

Needless to say, these freaks did not get a message in return. I did, however, exchange numbers and have a couple of dates already:

Date #1: A nice, home-grown kinda guy. Lives 15 minutes from his parents and has only ever been to Mexico and beach resorts. He was polite and we had a good enough chat, but in the end, he was entirely too white bread for me. When I explained where Korea was, he said, “Oh yea, the Vietnam War!”

Date #2: A construction worker with a child. I’m not wholly opposed to dating guys with kids because I’m nearing 30, but if you’re not the whole package, it isn’t worth it to me. He fidgeted a lot and I’m guessing that’s because it was 5:30pm and he was drinking an extra tall coffee. Relax off the caffeine. I texted him afterward telling him that I wasn’t sure we were compatible. He apologized for being a douche.

Date #3: This guy texted me that afternoon and made a plan…2 hours before we were meant to meet up, he cancelled and asked for a rain check. Before almost every first date I have, I try to cancel and think of every excuse not to go on the date. I’m guessing he did the same, but I’m also assuming that I’ll never meet him in person to find out since he didn’t ask for another day.

Dates 4 and 5 are this week, so fingers crossed for no disasters and that I can actually meet a quality guy that I want to date. And, if he can be a traveler who’s smart and can spell that would be a plus.

Confession: I am a Dating Dumb-Dumb

I graduated in the top 10% of my high school graduating class, cum laude from undergrad, and with a 4.0 in my Masters. But this post isn’t one bragging about my accolades, it’s actually quite the opposite…I may be smart in school, but I am dumb when it comes to guys. I’ve dated cheaters, hillbillies, heartbreakers, and liars. I’ve also dated nice guys, of course, but no matter who they are, I suck at dating them. I get jealous, I worry that I’m not good enough, and I want attention that they’re not willing to give (and not in the attention whore kinda way). 

Hence one of my New Year’s resolutions: chill the f*ck out. My brain is running on constant mode, which means I analyze every situation with a guy. Will he call? Does he like me? Am I being too overbearing? Why hasn’t he drawn me a picture in Draw Something?? 

This is why my friends tell me to date multiple guys at a time. You can’t fret as much about multiple guys because you won’t have the time. My theory is a bit different: when I find the right guy, I won’t need to fret because he will call, he will show that he likes me, and he will draw me pictures. This guy doesn’t have to be Mr. Right but should be the right guy for right now. 

Now, the trick is finding this “right” guy. In the past, I’ve met guys at bars and through friends…I’m still single, so you can see where that got me. But because both of these methods are the “traditional” way people meet, I’m still willing to try. Online dating is also still going strong out there in the world, but that makes me nervous and I hate picking out profile pictures. Also, paying to find a date is against my moral code (for this month anyway). 

I want it to be easy. (While looking toward the sky)…please let someone fall in my lap who likes my quirky style, the fact that I’ll blog about him, and will wash dishes. 

I read an article once where a girl interviewed all of her exes to see why she wasn’t “marrying material.”  She was surprised to find out that all of the reasons why she thought they’d broken up were vastly different than the reasons the guys had thought. After reading that, I’ve always wondered what my exes would say. First, I have most of them on Facebook, so a simple message of “mind meeting up to tell me why I sucked?” would be in order. Then, the grueling question and answer sessions would follow. I’d cringe, probably cry, and hopefully learn a lesson or two. With said lessons, I’d be prepared for what I need to do differently next time, for the “right guy.” 

But, until I get the courage to email every ex I’ve ever had, I’ll stick to winking at bartenders over martinis, rubbing elbows with hotties on the train, and looking toward the sky praying a good one will fall down on me.

Karma Came and Got Me

A few days back I wrote a blog curious about why guys take phone number and don’t call them. Well, the universe read said blog and both guys I’d written about texted me within a couple of days. I decided to go on a date with one of them (the biker who randomly stopped me on the street) and let’s just say it didn’t go so well. On my way home, thanks to my handy phone transcriber, I made a list of the words that came to mind…

short * self-righteous * presumptuous * florist * biker * grabby * self-conscious * bodybuilder * veiny * full of himself * unsettling * awkward * strange * corny * silly * goofy * horny * confident * annoying * pompous * pretended to use carrot as a tongue * karma came to bite me on the ass * complimentary * kept calling himself cute * drunk * alcoholic * immature * said, “I will lead you to the Lord” * hypocrite * persistent

If you couldn’t tell from this very awesome list of words, I will not be seeing this guy again…

Taking a Girl’s Number

Hey, I just met you

And this is crazy

But here’s my number

So call me, maybe?

-Carly Rae Jepsen


“Why do guys bother to ask for a girl’s phone number when they have no intention of using it?” I asked.

Kira began, “Maybe there’s a secret—”

“Society of douches,” I interjected.

“Ha! No! Maybe there’s a secret game that guys all play trying to collect as many phone numbers as they can.”

Maybe Kira is right or maybe guys really are just douches, but what’s the point of asking a girl for her phone number if you aren’t going to follow through? Just because I’m leaving the bar, it doesn’t mean you need to pretend you’ll call me. Just because you ride past me on the street, it doesn’t mean you need my number.

Yesterday I was stopped while walking along the street by a rather attractive guy riding a bike. He stopped mid-ride to strike up a conversation, asked me to get drinks with him (which I politely declined because I was leaving town that night), continued asking me questions, and finally asked for my number so we could get my favorite food for dinner some night.

The idea put a smile on my face and I randomly giggled for the rest of the evening about how a cute boy had asked me out. But will this alleged phone call actually take place? If not, I don’t mind, I swear, there are plenty of attractive fish in the sea, but if the biker had no intentions of making contact why did he even ask in the first place? (Unless, of course, he’s going home to brag to his friends that he can add another tally to his ever-growing list of gal’s digits that he’ll never use.)

Now, I’m not making presumptions about said lad, but merely speaking from experience. For example, last weekend I was at a bachelorette party where a cute 20-something sporting a sweet smile and a yellow sweater began making conversation. We talked for about a half hour before my party train was going home, but before I left, Mr. Yellow asked for my number. There was no prompting by me, but an outright, “Can I get your number so we can hang out sometime?”

That was Saturday, today is Wednesday. No phone call, no text. Now, it’s fine that he didn’t make contact. My feelings aren’t hurt, but why ask in the first place?

This same scenario has happened to me more times than I can count (which is probably why I no longer hold my breath waiting at the phone). I am tired of reciting my digits for attractive men (must admit, never thought I’d say that!). If someone says they’re going to call, can’t they just…well, call?

I’m not planning on hearing from either of the aforementioned guys, but if I do, I’ll be sure to congratulate them on having some cojones to take the second step…that whole crazy following through thing. Don’t bother with step 1 if you’re never planning to do step 2. Please and thank you.

Hello Universe

To: Universe

From: Ashley

Subject: Settling Down

Most people I know are settled down – whether it’s in their role of parent, wife, teacher, husband, Sycamore resident, etc. I am definitely not one of those people. And honestly, the idea of settling is a bit unnerving; it’s committing to something or somewhere or someone for forever. Since I left for college at 18, I have yet to find a place to call my own or a man to call my own – mine forever. Despite it being a bit scary, settling down is the recurring thought that permeates my before-sleep-thoughts and my dreams. I picture my life in the future while waiting for sleep to come and it always involves me being in love or married and with the perfect job.

I don’t think I’m scared to settle down, I think it’s unnerving because it’s something I’m afraid I’ll never get. Yes, I know most of you reading this are rolling your eyes at my pessimism and having your fingers prepped to say, “Of course you’ll fall in love with a place and with someone!” But my roving mind has yet to find a place that feels right for me or a guy who likes me more than I like him. In less than a month, I’ll be 29 and in those 29 years I’ve lived a blessed and happy existence. When I think about major complaints regarding the last 3 decades, I don’t have very many…except for the fact that I’m ready to fall in love with a town and with a guy. I’m ready…the open door is here and I’m ready. Without a concrete future life plan, now is the perfect time. Maybe I had to live my great life and give my wandering eye and wandering brain some attention before I knew that I was ready.

So, universe, I’m putting it out there to you: help me find my next step. Help me find who’s right and where’s right so this happy existence can continue while settling down (not settling). No more floating, no more roaming, I’m ready to be brought home. I’ll help, I’ll do what I can to make the process easier, but some guiding words or flashing neon signs would be nice too. Namaste universe.

Quit Playin’ Games, Fool

Even as a kid, playing games wasn’t really my thing.  No dodge ball and definitely not Nintendo. Boys, on the other hand, loved games…and judging by the guys I’ve met and/or dated in the past few years, they still love to play games – only now it’s with girls’ hearts. It seems like almost an impossible feat for guys to be open and honest, for them to fall in love or at least be open to the possibility of it.  What happened to the days when you said what you felt and you did what you said you were going to do?

At 28 years old, I’ve dated my fare share of guys, with a rough estimate of 80% of them who aren’t honest about what they want or what they’re feeling.  If you know me at all, you know that honesty has never been a very difficult task for me (in fact, I’m a terrible liar!), so when I give someone my honest feelings, I expect the same courtesy in return.  Guys, is it so hard to express your feelings? Does a cat really tear apart your tongue every time the truth tries to escape?

Maybe the reason I keep meeting game players is because they aren’t the one. The right guy for me will call when he says, text when he’ll be late, send flowers when he misses me, take me on dates, ask me questions and listen attentively; he’ll be open about his feelings and won’t shut out mine.  And he’ll do all of this because he wants to, not because I ask him to.  I don’t play games and I don’t want my man to either (unless of course it’s baseball).  And if he does, he ain’t the right man for me.  Been there, done that, lost that game more times than I dare to admit.