The Dating Game (Part I)


I have decided to do something that I have never been able to do before: Date. I am loyal to a fault, and because of this I have never been able to date more than one person at a time. Obviously this hasn’t been working for me, so why not play the field? It’s not like I’m going to have a relationship with every guy I meet, or even go on second dates. It’s time to get out of my comfort zone, take chances, and meet new people.

When I go on a first date with someone, I put a lot of pressure on it. I come into the date with unrealistically high expectations of how the night is going to go and what kind of connection I am going to have with the man I am on a date with. I expect kindness, chivalry, laughter, and intellectually stimulating conversation with a side of sexual chemistry. Being the analytical person I am, once I am on the date I start picking the other person apart and asking myself questions about the connection. Am I attracted to this person? Do I see a future with him? Do we have enough interests in common? Will my family and/or friends approve? Is he being inquisitive enough about my life or just talking about himself? Why am I picking this person apart? This is unnecessary pressure for the first date and I need to stop this behavior. I don’t believe in “love at first sight”, so why am I expecting love on the first date? I believe in lust at first sight and that a true, intimate connection comes with time and getting to know one another, but how can I get to know someone if I am not giving them a chance? Damn these double edged swords… I have had a bad habit in the past of going on dates and, if I don’t feel a strong connection (even if they are a decent guy), I don’t give them a second chance to see if we could be compatible. I have finally come to realize how unfair this is.

Any time any of us go on a first date we are all nervous, and nerves are a funny thing. They can cause you to be someone completely different than who you really are; they can make you talk way too much about yourself trying to impress the other person, thus making you come off as arrogant; they can make you extremely shy and not say anything about yourself and come off as boring or uninteresting; they can even make you try to be someone who you are not on the first date to morph yourself into the person that you think your date will be attracted to. First impressions definitely mean a lot but, factoring in the nerves, we all deserve a second chance sometimes to make an impression.

So why have I been cutting things off at one date if I don’t feel that strong initial connection? On the flip side, when I do feel a connection I immediately stop talking to anyone else that I was pursuing, or who was pursuing me, and give that man my full attention and energy. But why am I doing this? Men always keep their options open and date more than one woman at a time, so why can’t I play the field a little?

The first step in dating and meeting new people for me was to join dating apps. I’ve tried Plenty of Fish,, and eHarmony in the past and wasn’t a big fan of those websites. They are too much work and in order to make it worth your while you have to purchase a membership (which isn’t cheap!). Plenty of Fish is free, but good lord there are some creepers on there! My friends kept talking about how cool Bumble is, so that was the first app that I joined.

The way this Austin-based app works is that you log on and set basic parameters for what you are looking for: age range and distance radius (in miles). This is extremely easy and, unlike the big websites, there aren’t a million questions that you have to answer to match with someone. Once you’re done with your settings, you create a profile for yourself with up to 6 pictures and a very short bio. Then let the swiping begin! Snapshots of users come up for you to sort through and if you’re attracted and interested in the person you swipe right, and if you’re not you swipe left. Easy, right? I liked it. It is simple, basic, and the best part is that once you mutually match with someone by swiping right, the girl is the only one who can reach out to initiate the conversation. This saves women from being bombarded with messages from creepers and people that they are not interested in. This was a refreshing change from the other websites where any man can reach out to you, regardless of if you are interested in them or not.

The Tall Man

After just 3 days on Bumble, I matched with a man and we decided to meet. We went on a few dates, and we were actually having a great time! He was kind, chivalrous, handsome, 6’5″, and would actually call to ask me out on dates (yes ladies, chivalry is not dead). I felt a great physical and emotional connection with this man; he made me laugh, we had a lot in common, and I could be myself around him. This gave me hope that there are still great, single men out there. I did what I always do though; I immediately stopped talking to the other men on the website, gave him my full attention, and even deleted the app.

I really started to like this guy but, unfortunately, he was not ready for a serious relationship as he got out of a toxic relationship just a month and a half prior to meeting me. In his words he said, “I just need to do me right now”. I got it (I’ve been there before) so I wanted to respect his needs and feelings, but I wasn’t about to wait around for him to be ready (although the former me would have). So then I was kicking myself. This wasn’t the first time I’ve heard this. Why didn’t I keep my options open? Why am I so loyal to the other person when they haven’t earned that loyalty? That was it. I was not going to let this happen again. It is this unnecessary pressure I am putting on relationships that has caused me to make a change to my approach and just be OK with dating more than one man at a time. So I turned back to my dating apps.

Next up: Tinder. For some reason I thought that this website was for hookups only (don’t get me wrong, there are plenty of people on there for hookups) and it had a very negative connotation. The other week, for fun, I decided to check it out because why not? It is very similar to Bumble in every way except that either person can reach out once you match. To my surprise, I actually liked this website! It is nice to be pursued by men who initiate the conversation, but also Bumble had given me confidence to initiate conversations myself. In just 2 days I had over 20 matches and 10 conversations going with men. Then the date invitations started coming in. My confidence was back and I had 3 dates lined up for the following week/weekend!

The Swimmer

Date #1 was a lunch date with a swim coach that lives in San Antonio. We were to meet in San Marcos at a cute café. He was very sweet, texting me every morning wishing me to have a good day and was very persistent. Through the texting I began to notice his grammar. He kept using “your” where he should have used “you’re”. At first I gave him the benefit of the doubt and chalked it up to it just being a typo, but then it kept happening: “Your a very busy lady.” Bad grammar is one of my biggest pet peeves, so I called the date off. Maybe I overreacted a tad, but I couldn’t help it! It was extremely annoying. I am definitely not alone with this pet peeve! You wouldn’t believe how many people out there are equally turned off by bad grammar. Unfortunately, this wasn’t the first time I had turned down a date because of bad grammar and it may not be the last. Men, take note: Your grammar is very important when you’re trying to attract intelligent women.

The Canadian

Date #2 was actually the same day as date #1, but later on that night for drinks. Two dates in one day? I’m starting to live on the edge! This date was with a manly, very intelligent, well-spoken, well-traveled, Canadian man. We met on West 6th street for a couple drinks and conversation. I actually had a great time! We had a great intellectual connection, and he was very rugged and handsome. Then it happened again; I began to catch myself picking him apart like I always do.

Towards the middle of the night I kept noticing that I was spending the majority of the time listening to him and not talking. He would ask me a question about myself and then, as I was answering it, he would be reminded of something else from his life experiences and take over the conversation again. 15 more minutes of me sitting and listening. As interesting as his stories were as a result of his exciting life experiences, I couldn’t help but think that he was a little arrogant. I was getting to know A LOT about him, and he didn’t really know that much about me. I began to get frustrated from being cut off and not being able to finish my stories.

However, he was very kind and chivalrous, pulling my chairs out for me and opening my doors, and he even put his scarf around my neck to help me keep warm as it was a chilly night. Then I thought well maybe I’m over-analyzing again and maybe he’s just talking a lot because he’s nervous. So I decided to give him the benefit of the doubt and go on a second date to find out more. I made a promise to myself that I was going to go into this with an open mind while keeping my other options open in case this new matched crumbled.

I did it again. I freaked myself out, picked the night apart, and called the second date off. The worst part was that I realized that I was doing the one thing that frustrated me about dating; I led him on and flipped the switch. I felt awful.

When I called off the date he had no idea what happened and was completely stunned. I decided to tell him the truth about what made me change my mind. Not only did he control almost the entire conversation, but at the end of the night he got a little too physically aggressive for my taste. Men, take some advice from a single woman: Don’t try to sleep with a girl on the first date (or even lead her to believe you want to) unless you’re both just looking for a hookup. If you want to have something real, take it slow. Give her a nice, sweet kiss at the end of the night, or don’t kiss her at all and leave her wondering how you feel and wanting more. Ladies: this goes for you, too. Don’t give the milk away for free!

The Procrastinator

Date #3 got postponed (probably forever) because I didn’t have room in my extremely busy schedule to meet up that week. Plus, he kept asking me out the day-of, and by that time I had already made plans. This is another thing that will make a woman lose interest in a guy pretty fast.

One last piece of advice for the men out there: If you’re pursuing a woman that is worth your time and efforts, book the date in advance. Don’t wait until the last minute because if she’s independent, she’ll already have plans. Also, if you initiate the date, plan it. Pick the spot and time to meet up and show the woman that you can take charge and make a decision. She will appreciate this effort. If she doesn’t want to commit to near-future plans with you, sorry guys, she’s just not that interested.

Well, another one bites the dust and on to the next…

“Nothing worth having comes easy.”


3 thoughts on “The Dating Game (Part I)

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