Tag Archives: awkward dating

It’s Not Me; It’s You

I’ve had this idea in my head for the last few years that if I could just find a nice guy and have a really great date, that everything after that would come naturally and just fall into place. That idea was incorrect.

In any relationship, there’s a time where you have to figure out if you want to move from casual dating into something more serious or if you should call it quits. When I was younger, this transition was pretty easy – mostly because I completely skipped the first step. In middle school and even high school, “Will you go out with me?” really meant “Will you be my girlfriend?” There were still some awkward dates (especially when your date’s mom has to drive you around), but it was ok, because those dates were safely in the framework of a relationship, and instead of worrying about your “status” you could just focus on getting to know each other. In college, I had a lot of weird dates, but as soon as I found someone I really liked, it generally went something like “I like you. You like me. Let’s stay together for the next 3-5 years. Okay. Cool.”

Dating in my 30s has been a completely different ball game. At first, my main problem was just trying to find an interesting guy to have dinner or a drink with. I met a good number of creeps, and I kept thinking, “I just need one good date! Just one!” Then I had a great date, and another great date, and then a not-so-good date, and then he disappeared. Unfortunately, this pattern has more or less been repeating itself for the last couple years over and over again.  I meet a great guy, we have a great time, they seem really into me, and then for reasons that are never entirely clear, they (usually suddenly) change their minds. Because I’m human, I’ve been taking this personally. Am I not pretty enough? Did I always have food in my teeth? Did he get back together with his ex because she’s better than me? Do I laugh too much? Am I too laid back? Did I talk too much? Did I not talk enough? You get the idea. Obviously, this is not a great mind set to be in. Nobody wants to be constantly second guessing themselves, and it’s certainly not attractive. I’d go back through our dates, and I wouldn’t be able to think of one thing I did that would make them suddenly change their minds. I kept saying to my friends, “They liked me 3 weeks ago! I’m the same person I was then! What did I do?”

It’s taken me a long time, but I finally realized the answer: Nothing. I didn’t do anything wrong.

I have some working theories as to why this is happening so much more in my 30s – one of them being that the stakes are much higher now. Once you make that transition from a few dates here and there to dating exclusively, shit gets real. A lot of people in their 30s are ready for marriage and/or kids or at least a long-term relationship, and that’s scary. What if it doesn’t work out? It’s a lot easier to back out after 3 weeks then after 3 months or 3 years. Sure, relationships are scary, but I’d rather spend the time to get to know someone I really like and THEN decide if we think it will work long term than not even give that person a chance out of fear.

But, that’s just me speculating. What I do know is that I don’t know what they’re thinking. I don’t know their past relationships or what’s currently going on in their life or any of the million other things happening that have absolutely nothing to do with me. It’s disheartening when something with promise fizzles. It’s especially frustrating when you think you’ve been misunderstood, judged unfairly, or not given the chance to open up. It sucks, but 9 times out of 10, the circumstances are beyond your control. I’ve spent a lot of time beating myself up over things I have no control over, and it’s oddly liberating to finally accept that sometimes there is just nothing I can do.

At the beginning of this year, I was feeling pretty low. I was texting with my mom and I mentioned that I was really sad, but I was sure I would eventually be fine. My mother, in all her loving wisdom wrote, “You are right. You’ll be fine. You won’t feel fine all the time, but you will be fine because you’re not in control of other people’s reactions, and you have no way of knowing exactly why they act as they do. It probably has nothing to do with you most of the time. That doesn’t take away the sadness and frustration, I know. But the plan is for good, not evil, to give you a future and a hope.”

It’s been hard over the last few months/weeks/days to remember this, because it IS sad and frustrating, but ultimately, her words have been the best advice in the world. I don’t know why people act the way they do. I can beat myself up over it, feel slighted, grow bitter, or I can keep trying to be the best version of myself and be confident that the plan is for good, not evil, and I have a future and a hope.


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2015: My Noble Search for True Love

I’ve recently been reading Mindy Kaling’s book, Why Not Me?, and I’ve realized that Mindy and I have a lot in common. Well, except for the part where she’s a successful comedy writer living in LA with beautiful skin who gets to regularly make out with Chris Messina. But, when it comes to men, we’re looking for the same thing: “I just want a boyfriend who is sweet and trustworthy. That’s it. And no neck tattoos.”

It seems like a pretty simple and reasonable request, but my search for this sweet and trustworthy boyfriend has been a pretty tumultuous one. The best and worst thing about dating is the roller coaster of emotions that come with it. There’s the nervous excitement before the first date; the constant checking of your phone to see if he’s texted yet; the minor heart attack after hitting “send” on an ill-advised text; the jubilation after a date finally goes well; and then the constant state of nervousness during the first few dates wondering if this is really turning into something or if you are just being punk’d. And, of course there’s the crushing disappointment when he doesn’t call, or when he’s nothing like you expect, or it just falls apart for no real reason.

In looking back over my year, what I mostly remember is all the small ups and downs of my dating life, and how exhausted I am. Since I don’t have any particularly awesome major milestones to look back on, I’ve decided that instead, I will recap my year of dates. Get ready for a bumpy ride:


January: The year started out great. Ohio Against the World. My Buckeyes won the National Championship, and I watched all of the playoff games with my boyfriend. I was finally in a real relationship and very optimistic about the future.

February: Things are good. My boyfriend and I have really cute Valentine’s day plans, and although they don’t quite go as expected, I’m still optimistic.

March: I get dumped. In a very cruel and hurtful way. I realize my “relationship” was a giant joke. I don’t really remember much else about this month.

April: Newly single and sad, I hang out with my friends as much as possible.  At the end of the month, I invite myself along to a guy’s night at a video game bar, and I meet a guy! He’s very drunk and I’m pretty sure he won’t remember meeting me, but it’s ok because I’m back in the game!

May: Guy’s Night Guy remembers me! We go on a date, and although I cry on the way there thinking about how much I hate dating, once I’m actually on the date, I realize that Guy’s Night Guy is sweet and funny and immediately puts me at ease. We continue to date for the rest of the month.

June: June starts off pretty great. I’m still casually seeing Guy’s Night Guy (GNG), I go on vacation to Mexico, and life is looking pretty good compared to a few months ago.

July: Minor set back. GNG tells me he’s not sure he wants a relationship and goes across the country for a month on vacation. After he leaves, I join Tinder. My life is changed forever. “Playing Tinder” takes up a lot of my time, and I even get most of my friends to play it for me. I talk to a few guys (including a psycho who only wants to meet me if I agree to come to his house), but one in particular seems very promising. He’s a vegetarian skateboarder who thinks I’m adorable. We have a pretty magical first date, and the next few dates are just as good. We plan a fun weekend together, and then…. he never shows up. I don’t hear from him again. I vow never to date a vegetarian.

August: GNG is back! Woo! Things are great! I also meet a very tall, large man I refer to as the “Viking.” The Viking is hilarious, and we have three amazing dates full of lots of beer, hot dogs, tots and trivia. Then… I don’t hear from him again.

September: GNG and I are still hanging out. Since I am an excellent communicator, I have an awkward, unclear conversation with him about the status of our relationship, which I grossly misunderstand.

October: A few significant things happen in October. First, I think that GNG and I are exclusively dating until my friend sees him on Tinder (which I no longer think is fun). This leads to another totally awkward conversation where I realize that while I thought we were a couple, he did not. We then (and I really don’t know how) come to the conclusion that we should keep dating but also “explore other options.” So, I explore other options. I call the cute boy I  met a couple weeks earlier, we have a great first date, he tells me he had a great time, and then… I never hear from him again. I then go on a date with a guy who offers to clean my apartment naked. He never hears from me again. I turn 33. I go on a date with a 26 year old who “vapes” and tells me lots of weird, racist stories. He never hears from me again.

November: November starts off with another first date. This first date lasts past midnight on a weekday, and we continue to date throughout the whole month, bonding over comic book shows and emo music. I was feeling optimistic once again. (Also during this time, GNG slowly stops talking to me completely.)

December: Emo guy stops talking to me. I do eventually get an explanation that is mostly him telling me how he’s WAY not over his ex. I pull my hair out. Right before Christmas, I go on a date with a guy who sounds pretty perfect on paper. However, in real life, he is a hyperactive crazy person who is in love with his cousin. As a last-ditch effort, I agree to meet a guy for an afternoon drink on New Year’s Eve. He is 5’2″ and never stops talking. I left around 8 to spend New Year’s Eve with my friends – where I probably should have been all along.

The End





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Dating: I think I’m doing it wrong

You know how sometimes, in the movies, the protagonist is divorced or widowed and decides to start dating again and they realize they don’t know what they’re doing? They say something cute like, “The last person I dated was my wife, and I was 18. I don’t know what I’m doing any more! The game has changed! How am I supposed to do this?”

I feel like that. I have no idea what I’m doing.  But unlike our movie protagonists, I have no excuse. I never left the game. I’ve been here all along. Yet I still feel like it’s somehow left me behind. It’s changed, and I can’t keep up.

A few weeks ago, I was hanging out with a group of friends (most of them married), and naturally, I started talking to the only other single person there (a guy). In the morning, I got a text from one of my friends that said, “So, how did it go?!?!” Confused, I wrote back, “Good. I went to sleep.” When I talked to my friend later, she questioned me more. She couldn’t believe nothing had happened with us and asked if we had at least exchanged numbers. While I had enjoyed talking to him, the fact that he might be interested in something more than just pleasant conversation hadn’t really occurred to me. I told my friend that I had just said goodnight and that was it. She shook her head and said, “Ellen, he could have been trying to kiss you – literally leaning down, trying to kiss you — and you wouldn’t know.”

She’s basically right.  I’m oblivious.

In college, I was at a small party where I didn’t know very many people. There was a group playing cards, and an older guy — who I knew, but not very well — asked me if I wanted to join in the game. I was thankful for the friendly gesture, but told him I didn’t know how to play.  He kindly offered to have me sit with him, and said he’d help me learn how. It was a card game, so it wasn’t too complicated, and I caught on pretty quickly.  Although I knew what I was doing after a few minutes, the guy stuck around – continuing to give me tips, offer advice, and make conversation.  Unfortunately for this guy, I happen to be super competitive.  I didn’t agree with some of his “tips,” and I wasn’t about to let him ruin my chances of winning. So, I politely told him that I understood the game and that I could take it from here. Then I promptly ignored him until he left the table and went into the other room.  I had no idea that he was actually interested in me, and was just trying to get to know me better until days later when a friend told me.

I won the game. The guy went in the other room and struck up a conversation with a girl who didn’t ignore him, and who he later ended up marrying.


Although I often have no idea what’s going on, this can sometimes work to my advantage. For instance, if I don’t know someone is interested, then chances are I wont make (as big a) fool out of myself. I promise that I’m not normally ridiculously socially awkward, but stick me on a date, and it’s like I forget how to make sentences.  A couple of weeks ago, a guy asked me the totally normal question of “What do you like to do for fun?”  There are many normal ways I could have answered this question, but instead I panicked. So, instead of something like “reading” or “baking” or “watching movies” I said, “I guess I like to drink.”

Seriously. I said that. Hi, I’m Ellen. I’m a lush.

The problem is that even when I think I get it right, I still end up missing something. A few weeks ago, I met a guy who I thought I was interesting, funny, and good-looking. We talked most of the night, I don’t think I said anything too awkward, and when the night ended I was feeling very good about the whole thing. He pulled out his phone, presumably to get my phone number, and then he asked me… wait for it… to be Facebook friends. I’m not joking. Is that even a thing? Am I that out of touch? When did that become ok? No, I don’t want to be your Facebook friend. I want to be your real life friend. I don’t want to read about what music and movies you like, I want you to tell me what movies and music you like, preferably over dinner.

Needless to say, I never hung out with him again.

I’ve had (maybe more than) my fair share of bad dates, awkward conversations, missed opportunities and crossed signals, but I’ve also had some good, really fun dates, and met some pretty awesome people. So, even if I don’t know what I’m doing, I guess I’ll continue to at least pretend I have a clue and hope for the best.

Wow. Lots of feelings. Don’t worry, I’m baking them into Espresso Chocolate Chip Cookies, so keep a look out for the next post.

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