Three Dates in Ten Days

Dec 23, 2013 by

          “What is Santa bringing you for Christmas?” my co-worker innocently asked.

          “Well, I would love if Santa would bring me a boyfriend, but that seems a little unrealistic,” I responded to him with a cheerfully bitter tone and a smile.

          Yeah, I casually throw my dating woes out like this to people.




          My date recaps for friends tend to begin as follows:

          “How was your date?!” they’ll excitedly ask me.

          “Oh, right,” I’ll unenthusiastically start, “he was alright –”

          “But?” they’ll interrupt me with a how-typical tone and an accompanying eye roll.

          “I wasn’t attracted to him,” I’ll shrug.

          “Why weren’t you attracted to this one?” they’ll question.

          “I just wasn’t,” I’ll apathetically answer, knowing that I’m in for further interrogation.

          “Why? Why weren’t you attracted?” they’ll probe in frustration.

          As I’ve justified my lack of interest in the three guys I’ve recently gone on first dates with to my friends, I must also keep you, my lovely virtual friends, in the know. Feel free to refrain from grilling me for my pickiness. I’ve already been lectured enough by your real-life counterparts. Below are my explanations why these guys failed to blow me away. I’ve briefly mentioned two of them here, but didn’t provide much insight. Feeling that I owe y’all (I’m feeling country – deal with it) a legitimate dating update, I’m letting you in on the reasons why these guys are my non-Prince-Charmings.

          By the way, can we commend the fact that I’ve gone on three dates in the past ten days? Earlier this year, I went on only three dates in the time span of nearly three months. When I decide to do something, I am legit. Slash, when Valentine’s Day gets close, panic sets in. (In true procrastinator’s fashion, I have even left my boyfriend search to the last minute. To quote a cop that once pulled me over for tossing paper out the car window, “How can a girl that’s so smart be so stupid?”) Applause is definitely in order. (I hope you’re clapping!) On that note, so are nicknames. At this rate, we’re going to have a hard time distinguishing my dates without them, especially since I’m already having difficulty remembering their real ones.

The Debtor

          “I’m not interested in him, but I’m pretty sure he was into me,” I told my friends.

          “Obviously!” they exclaimed. “What uninterested guy talks to a girl until six in the morning and asks to see her the next day?”


          Two Fridays ago, I went out with a guy I met at my work Christmas party. With my boyfriend-by-Valentine’s-Day goal top of mind, a few of my married girlfriends and I were on the prowl. (Married ladies are the perfect wing women. Already wedded, they are generously charitable to my single case. To any other givers out there, donations are payable in boys.) Married man and the guy who drunkenly told me that I’m “fucking pretty” (how charming) in between asking my name four times (yes, four) aside, there was one guy that kept inviting me to join him and his friends on the dance floor. By the end of the night, he and I were chatting about Italy, where he had recently visited. FYI to any guy that ever wants my attention: talk Europe. It is the perfect topic to put me into a number-giving mood.

          Despite my clear readiness to relinquish my contact info and go (as per my own advice), this guy was not picking up on my obvious signs, such as showing off my non-smartphone, basically giving him a free pass to the ROM. Though I could tell that he wanted my number, he wasn’t asking for it and I was growing impatient. I gave up on waiting, and I met my friends outside after grabbing my coat. Two minutes later, he was out there talking to me. My legs about to be frostbitten and my mind highly aware that Valentine’s Day was little more than two months away, I forced myself to take action. I told him that he should take my number, since we wouldn’t see each other around the office due to opposite work schedules (slash, since he didn’t have the balls to ask).

          We went for affogato one week later. When the ice cream place closed at midnight, I drove him up to his car, because he had parked further down the street than I had. With him still talking, I pulled my car up to the side of the road to put it into park. Noticing this, he asked if I wanted to go somewhere else. Because the conversation was flowing with ease, I suggested the 24-hour Starbucks near our homes, unaware that I was foreshadowing a late night. At Starbucks, he talked to me until close to 6 am. I thought I was going to pass out at the table. It was a Friday night, which means I had gone to the gym before work that day. I was coming up to 24 hours without sleep.

          After too many hours of conversation, he was getting too comfortable with his choice of topics, letting it slip that he owes money to multiple credit card companies, owes his mom money for his trip to Italy, and owes his cousin money for renting their basement that he had already vacated. I was immediately turned off. I’m not looking to get married anytime soon, but that doesn’t mean I’m going to set myself up for failure to get engaged by dating guys that have no long-term potential. Poor money-management skills not only show lack of financial sense, they also demonstrate limited responsibility and maturity. His bragging about frequently fighting (physically fighting!) with friends while at parties only provided further confirmation of his immaturity. When hinting at the time didn’t free me, I decided to clearly say that we should leave. Next!

The “Nice” Guy

          “He gave me the I’m-the-nice-guy-who-never-gets-the-girl crap. Does he expect me to pity him?” I complained to my friend during Passions, our regular lunchtime guy-update sessions. “I could tell stories about past shitty guys I’ve known that it hasn’t worked out with, but I don’t. Those guys have nothing to do with the one I’m sitting in front of in the moment.”

          My friend laughed. “That’s a really good point, and I agree with you; but, I’ve noticed that you have two problems when it comes to guys: you overanalyze and you’re negative.”

          “You’re absolutely right,” I concurred. “I overanalyze everything (my entire blog is an overanalysis), and dating is probably the only aspect of my life that I’m negative about. You can’t blame me, though. I’m 24 years single. I feel like it’s never going to happen.”

          “Oh stop! You’re still a baby!” she said as she waved away my near quarter century of singleness as no big deal.


          The night after my date with The Debtor, I went out with The “Nice” Guy, who I met through OKCupid. I had skipped over this one’s profile without sending him a message, because his summary focussed too highly on sex and casual dating. That is not what I’m looking for. When I got a message from him, however, I chose to respond. I reasoned that my profile clearly states that I’m looking for long-term dating, so he either read it and knows what he’s getting himself into or he didn’t read it. My guess was on the latter, but that’s his fault. After some back-and-forth online messages followed by texts, he asked me to have dinner with him, given that we’re both foodies. I don’t like going for dinner on a first date, because there are few means of distraction when a guy can’t hold conversation, which is unfortunately common. On the other hand, I love food, so trying new restaurants is one of my favourite things to do. It’s a big dating catch 22 for me. Too lazy to counter dinner with a creative idea, though, I agreed and suggested sushi, his favourite.

          At the restaurant, we were seated in a tiny room that contained only our booth. Cozy. No pressure! After almost four hours secluded together, I was able to best describe this guy as negative and insecure, two of qualities that I find extremely unattractive. I am an upbeat, happy person. I need someone who can match me. I want to be with a guy who likes where he’s at in his life; not someone who is looking for some chick to save him. Furthermore, I don’t do guys that lack confidence. Apparently, he lost girls to his friends due to always being the nice guy. This caused him to have to fake being an asshole to girls in order to get their attention, perhaps explaining the emphasis on sex in his online profile. Cry me a fucking river. I don’t have the patience to reassure guys. I want someone who comes self-assured, a guy for whom my compliments would simply be the sprinkles on his already well-iced cake and not the butter cream itself. Needless to say, I declined his texted request to see me again.

The Actual Nice Guy (no quotation marks of mockery required)

          “He was nice –” I began.

          “But?” my friend interjected.

          “He was a bit shy. I like confidence,” I reminded.

          “Aw! It was the first date!” my friend defended him.

          “I don’t want a guy that gets nervous on a first date. Secure guys are able to match my social confidence right away,” I explained. “However, even though there wasn’t a spark, there were no red flags either. It is so sad that I am considering going out with this one again – not because I’m interested, but because he didn’t give me any major warning signs, like large sums of consumer debt,” I joked. “He did call to ask me out,” I added. “I don’t remember the last time a guy called me before midnight to ask me out. Even better, he called when he said he would.”

          “That’s a green flag!” my friend encouraged. “I think you should give him a second chance.”


          Like The “Nice” Guy, I met The Actual Nice Guy through OKCupid. My first impression of him: bad spelling and grammar. I decided to overlook it, having received a lot of feedback from friends lately about how incredibly picky I am. (I stand by my standards, peeps!) I can think of people I know that can’t spell or punctuate to save their lives but have lovely personalities, so I gave him the benefit of the doubt by responding to his message.

          Last night, we went for drinks and appetizers. He was definitely interested in me; I was definitely interested in the guy serving the table beside us. He showered me with compliments. I handle compliments well, usually responding with a cute/cocky hair flip, a smile, and a thank you. Unfortunately for him, there is such thing as overkill, and his kindness was murderous. According to this guy, I’m pretty, fit, different than other girls (I know, I know, but don’t tell me that yet!) – blah, blah, blah, blah, vomit. I like to be complimented (who doesn’t?), but I prefer when guys execute flattery sparingly and with some cheek. I like when people joke with me so that I can do the same. I like guys to have enough confidence to know that it’s okay to be playful. I enjoy guy-girl interactions that go a little something like this one from early September:

          “I need to finish my glass first,” I told the guy from Niagara, pulling away slightly after he kissed me. “Once you and I start, we don’t stop.”

          With his lips barely parted from mine, he smiled and remarked, “You need a little more wine in you for this, huh?”

          “With you? Absolutely,” I smirked.

          “Hey!” he said in a fake tone of surprise. “That was mean!” he laughed.

          I shrugged my shoulder and downed the rest of my wine. “You know that I think you’re cute,” I reassured him before leaning back in.

          Quite the opposite, The Actual Nice Guy gave off a desperate, please-like-me vibe that made me feel like I had to be sensitive to his feelings (ew) by staying far away from all forms of satire, sarcasm included (what is conversation without sarcasm?). Although I don’t do douchebags, I also don’t do too nice. (The implications of relativity entertain me. If a guy I was interested in said all of the things to me that this guy did, I’m certain that I’d be smitten.) How can someone speak so highly of me upon first meeting? Take it down, bud. While he was inviting himself to Europe with me (I’ve heard that line before. It’s a lot more effective atop bed sheets, but bullshit is bullshit. Truth: I’m a little scared that this one wasn’t bullshitting.), I was still on drinks. After an evening that wasn’t as bad as I’m making it sound, he insisted on walking me to my car. I’m a big girl, but okay. I guess that’s nice (my finger is virtually down my throat in disgust as I laugh about how I would melt if a guy I liked did this). It’s not like he was killing my chance of talking to that hot server or anything. – Oh shit, hardcore guilt is setting in as a result of everything I’ve said about The Actual Nice Guy. I totally mean all of it, but he was genuinely sweet. When he asks me out again (because he will), I’ll have to seriously think twice before rejecting him in order to absolve my guilty conscience. Like I told my friend, there were no red flags.

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