If you’ve read one blog post or you’re an avid newcitylifeadventure.com reader, you’ve most likely noticed that my dating life is dismal. I try, I really do, to take advantage of every situation where I can meet interesting and different people; I’ve tried the likes of OKCupid, Plenty of Fish, Tinder, speed dating, speed friending, Grouper, meeting guys at the bar, etc. all of which have given me disaster after disaster. Is it me? I am the common denominator in all of these situations. So instead of taking matters into my own hands, I decided to put matters into the hands of my bestie, Kira. Here’s how it went down:

I bought a month’s worth of match.com and asked Kira to essentially “be Ashley” for the month. I made my own profile complete with my pictures, my answers to questions, and information all about me. My username and password were then forwarded to Kira who did the searching, the “winking”, the chatting, the messaging, and the vetting. When it came time to exchange numbers, I went online and reviewed: was he someone with whom I wanted to go on a date? Once my phone number was given, the rest of the work came back to me. Within this month, I went on first dates with four guys, second dates with three of them, and a handful of dates with one of the original four. There was no love story in the end, but I did learn a thing or two about dating multiple people at the same time and not getting too eager about one nice guy.

I asked Kira to share her experience for this post:

Continue reading A Social Experiment →

Growing up, us girls watched the likes of Cinderella, Snow White, and Belle fall in love with a man whom she barely knew and live happily ever after. Books I read, movies I watched, and shows on TV all portrayed love as this perfect, easy task. Find a man and he’ll instantaneously fall in love with you. It wasn’t about lust, it was about serendipity. Fate brought us together and no matter where I am in my life, you and I are going to work out forever and ever. Maybe a few missteps will get in our way, but in two hours or less, our destiny will be sealed. So with all of these portrayals of love surrounding me for the last 30 years, it’s no wonder my ideals of a man and a relationship are skewed.

A great blog that I’ve mentioned before, Forty Days of Dating, explained this quite well: “Jessie wants love. She just wants to be a great girlfriend and to take care of her man. It just seems like she wants the perfect prototype to slide into her perfect boyfriend role.”

But that perfect boyfriend role doesn’t exist. Or if it does, I certainly haven’t found it, so it must be pretty illusive. I’ve met plenty of nice men who could be a Prince Charming if they tried hard enough or cared enough, but there’s always a flaw, something that makes me back away: he talks too much, he has bad teeth, he tries too hard, etc. So it makes me wonder, do I have a Princess Complex?

And I don’t mean that I act like a princess (though I’m sure a few people can attest to the fact that I have on occasion felt that pea under all those mattresses), but more that my idea of what I want from a man, what he can offer me, and how he’ll act is more fantasy than fiction. I’m looking for a prince, when they don’t exist. I have very high expectations for the men I meet and very rarely can they even come close to the standard that I’ve set.

So that leaves me with a few options: lower my standards, be a single old maid, or continue to date guys who can never match up to what I want. Two of the three of these choices suck big time. I am selective – some might call it picky – but maybe I am too critical and too harsh on the men I meet. Lowering my standards doesn’t mean they have to be low standards. Lowering my standards could mean, though, that I have the potential to meet men who aren’t princes, but can still be my Prince Charming.

As a last ditch effort before my time on Match expired, I threw my number at a guy with whom I’d had a few exchanges. We first met at a bar and had a four hour date discussing the perils of online dating, the ups and downs of living overseas, and the general get-to-know-you type questions. Yes, I said four hours – that’s a very long time in the first date world. I never once looked at my watch or hoped that it would please-just-end. Even without a goodnight kiss before my taxi pulled away, I was certain that date #2 would ensue.

And, I was right. Two days later, Mr. Wonderful asked if I was interested in having dinner…at his place. As a “renowned chef” (his words), he wanted to make a delicious meal before jetting off to Germany for two weeks. Though I’m always cautious about going to a guy’s place so early on, I agreed. He’d been perfectly harmless on date one; like I said, he didn’t even attempt to kiss me. He went all out on a four course extravaganza – it was splendid. Through the preparation, dinner, and afterwards, we talked about all sorts of things. As most second dates will do, Mr. Wonderful kissed me. I kissed him back. That’s as far as I wanted to take it. Kissing is a good first step. Why give away the cookie before he’s earned it?

I could tell that his hands were hoping to wander, so I gently pushed them away. He tried again and this time I vocalized that I wanted to keep the party PG. “This is PG,” he said while attempting to lift me onto his lap. I resisted, reminding him again that I wasn’t going any further. He pouted, but left me alone…for a few minutes. Another kiss came my way and I fielded it, but not fast enough for him to unzip my dress. Mind you, the zipper was a mere 6 inches (it was one of those pretty pink ones that are simply for looks and an aid for getting your head into and out of the dress), but within 30 seconds, he had already unsnapped my bra through the zipper opening.

“I said that we were keeping it PG,” I exclaimed whilst hopping up from the couch. Stalking to the bathroom, I noticed that the clock read 10:42 – a perfect excuse to leave on a Monday evening. I re-attached my bra, zipped up my dress, and stalked back out to the living room.

Putting on my sweater, socks (yes, he’d somehow managed to slip those puppies off, too), and shoes, I told him that it was my bedtime, so I’d be leaving. “But why?” he whined a legitimate I’m-three-years-old-and-want-a-new-toy-from-the-grocery-store-aisle whine. “Why stop something if it feels good?”

“Because I said so.”

“But, but…I made you dinner,” he reasoned. So by him making me dinner, he expected that I owed him sex?! On what planet were we? On planet Earth, no means no – always. He walked me downstairs, all the while huffing about the fact that we were having fun and that people always stop themselves from having fun. My arm flew up the second I stepped out of the door, “Taxi!!”

Near to tears, Mr. Wonderful neé Mr. Go F@$K Yourself tried one last time: “But I’m leaving for two weeks…” Exactly my point – why have sex or even get busy with a dude that I’m never – and I mean never – going to see again??

In case you didn’t already know this guys who’re reading this blog: no means no – always. And in case you didn’t know this, ladies, just say no when a near stranger asks you over; who knows what kinda shit you might get yourself into.

Revelations of the week

1. I just realized with aghast that while I sit here mindlessly looking at my Facebook newsfeed and getting annoyed with (*cough* jealous of *cough*) everyone’s baby and wedding photos, that I am just like you!! I never shut up about my dating life. My stories might not be as cute as your newborn or as stunning as your white dress, but it’s what I got, so thanks for reading 🙂

2. What I’m about to say will neither shock nor amaze you. I am a monogamist. A serial monogamist. But I’m not just into monogamy when I’m in love or in a committed relationship, I also prefer to date just one guy. After one date or two, I can tell if I want to continue to see the guy at hand and then will proceed to completely ignore any other guys on my radar. I’ve even gone so far as to quit the site where I’m yielding my radar after a couple of good dates. Is my love detector kicking in or am I going about this all wrong? For the record, this repeating feeling isn’t done out of free will; I’m like compelled to do this by some ulterior force. So simply stopping isn’t as easy as just saying no. 

But juggling guys is a very valid method of finding a mate, mainly because it would cause me to not be so obsessed with the “chosen one”. All of my attention wouldn’t be on one dude causing said dude to quiver with the fear of my biological clock ticking. Another great reason to date around is the fact that there are a lot of really great guys out there and if I’m spending all my energy on one great guy, there’s the possibility of even greater guys on the horizon. And if I don’t look, I can’t find ‘em. 

3. Is the real reason I want to find someone the fact that I want to stop searching? I am tired of going on first dates and continuously having to find new guys to date. Maybe I just need to take a break. For real this time. Just go out and do the things I want to do, then quite possibly a good catch will come my way when I least expect it. (Yea, I know, I’ve heard that one before, too…)

At lunch with a friend today, she made a very good point (as she usually does): If my blog is to serve as a chronicle of my life, my dating life is going to look sadly awful. What about the good stuff? What is the funny, happy, or interesting side of dating? And she’s right (as she usually is); I’ve had a really good time being single. I don’t love every minute of it and I don’t want to stay single forever, but my single life can be pretty exceptional.

1. If I’d married any of the guys I’d dated before I turned 29, my husband would most likely have been white. Now, there’s nothing wrong with that, of course, but because of online dating, I met a Latino. And now, I’m in love with the Latin culture. My experience with Latinos was limited pre-January 2013, so once the culture was introduced into my life, I’ve embraced it; I’m learning Spanish and I’m taking salsa lessons. I’ve eaten so much ridiculously delicious food in the last year and I can officially say that Cuban and Puerto Rican food are definitely a favorite of mine. Most importantly, I really like Latin guys. My match.com profile will definitely host a special search button for them.
2. Since I left small town America, I’ve met and gone on dates with guys from all around the world…Turkey, Ecuador, the Dominican Republic, Cuba, China, England, Scotland, New Zealand, India, and Canada. It’s super interesting to hear about life growing up in other countries and to compare our customs and traditions.
3. Because I date new people on a constant basis, I’m always getting the chance to try new places, eat new foods, and experiment with new things (i.e. salsa dancing). It’s been fun meeting new people with new tastes, favorite restaurants, and interesting hobbies.
4. Single life = single sports leagues! I’ve met some of my closest and newest friends in Chicago by playing S3, a sports league for singles.
5. Talking about boys is the most fun pastime for ladies. Even my aunts ask me about my dating life. My (married with a child) coworker hears all of my dating dramas and shares stories about her dating life before her husband. It’s all my girlfriends and I seem to talk about. What will we gossip about when we’re all married with children?!
6. My dating life has seriously gotten me the BEST blog material! If I didn’t blog about dating, I’d have a really boring blog…my kitchen is now painted blue…I made a new recipe last night…my husband plays his music too loud. Dating blogs are so fun and I get awesome responses from my Facebook friends! Thank you for that!!
7. One of my very first Sassy Hong Kong articles was about dating in the city. This one article catapulted my editing and writing experiences by putting me on the writing staff for Sassy and on the editing staff for CityLife magazine. I had so much fun in the publishing world in Hong Kong!
8. Lastly, I have some of the most entertaining first date horror stories ever. Get me at a dinner party and I have three amazing stories to get the ball rolling. In case you need a good dinner party story, here you go:

• Ear Licker
• Jessie’s Girl
• Angry Man

And while I really am ready to be in a real, committed relationship with a nice, normal, attractive (Latin) man, I can revel in the fact that my life is actually pretty damn good. I might not have everything I ever dreamed I’d have, but I certainly do have a lot for which to be grateful.

In all just seems so good the way we had it
Back before everything became, [algorithmic]

-Miranda Lambert (with a little help)

With a string of failed relationships bobbing in my wake, it’s needless to say that my dating life in Chicago has been less than glorious. When I look back on the last year-and-a-half, there are many bits and bobs to dissect: I realize that how I act in a relationship may need to change, and since my ability to give forth effort and love has at times been unrequited, I may need to reel this part in. But that’s not what I’m here today to analyze; instead, I’d like to focus on the method by which I’m meeting said disasters…I mean, men. In the past year-and-a-bit, I’ve dated guys that I met at a bar, through a contrived singles’ league, and from multiple online dating sites – a mix/match of both organic and algorithmic ways to meet others.

Now that I’m back on the prowl, I’m wondering which of these methods is best. Or maybe the answer is that either can work, depending upon the approach taken. In the past, I’ve met guys only on free dating sites – the key word here is free. I’ve tried really, really hard to not pay to meet a guy. But maybe these free dating sites are free for a reason…both cheap guys and cheap girls can get a cheap thrill. They aren’t for people looking to get serious. People who pay for dating sites are serious about finding love, amiright?

So once I choose a paid site (because apparently that’s where the “I’m ready to settle down” kinda guys are hanging out), my profile will need to be rather direct. Does this mean I should outright state that I want to get married and have kids? That way, there’s no confusion when in two months, I ask, “Where do you see this going?”

The second option for going about this dating thing is organically. To me, that means going about my regular life without my “searching eyes.” I’ve said this before, and I’ll say it again, the left hand is the 2^nd place my eyes wander on an attractive guy (the first place is his smile). So in this organic way, I need to just go about my business doing the things I like to do: yoga, salsa, maybe learn Spanish in a group setting, book clubs, volunteering, etc. Just be me and not worry about finding someone. “The right person will come along when he’s meant to…” says every married person ever.

The other part of organic dating is meeting guys through friends. I have NEVER met a guy through a friend. Now, that’s either saying something about me or saying something about my friends, and I hope that doesn’t mean my friends don’t think I’m worthy of dating their guy friends. So here’s my call to action – friends, don’t you know any single, funny, worldly, outgoing men who like to travel? C’mon now, hook a girl up! (I shall now step off my soapbox.)

In this rather crucial decision on where to go next in my dating career, I hope that my choice to be a grown up and pay for a dating site or to have fun doing the things I enjoy will pay off. Or they won’t and I’ll be that old spinster at speed dating. I kid, I kid.