The 8 Guys I Dated After My Almost Relationship (And Why They Didn’t Work)

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Vince Fleming / Unsplash

Six weeks after being dumped by a guy I wasn’t in a relationship with, I couldn’t keep him off my mind.

In order to distract myself, I used dating apps to meet people. Due to constantly traveling for work, I was really only home for about three of the six weeks. Somehow I managed to go on eight individual dates.

Here they are in order with the reason they each didn’t work.

1. The Felon Without A Car: While I had known that this guy had a rocky past, he seemed to have a decent personality, job, and was semi attractive. Little did I know that I’d spend the date listening to him talk about only himself, listing out extremely inappropriate details that shouldn’t be shared on a first date, as well as him implying he wasn’t chauvinistic when he clearly was. It turned out that not only had he taken the bus to our “date” but that he’d been in prison for something I didn’t care to ask about. He didn’t ask one question about me. Shout out to my friend for saving me from that terrible date. I couldn’t run out of there fast enough! He reached out the next day to ask when we could see each other again, and I politely responded that we couldn’t.

2. The (Slightly) Bitter Divorced Fella: This guy was so incredibly nice. Leading up to the date, we texted back and forth about everything imaginable. His failed marriage, my broken heart (pro tip, don’t talk about this kind of stuff before you meet someone), life expectations, hobbies, etc. Knowing what I knew about his past, I knew the two of us weren’t going to be compatible but went on the brunch date that he ended up paying for anyway. He continued to discuss his ex-wife in semi-bitter detail. It was very apparent that he wasn’t quite over the whole thing and probably wasn’t quite ready to date (but then again, was I?). While we weren’t a romantic match, I’d hoped that we could at least be friends. He texted a few times after the date, but then I think we both mutually understood that we just weren’t compatible.

3. The Young One: This is the guy you want to go out with if you need a laugh (and boy did I need a laugh after the week I had). He made me laugh the entire time at our dinner, but he also rushed me out of dinner so that he could head out with his friends afterwards. He was four years younger, had two roommates, and lived in one of the “younger” neighborhoods in town. While I think he’d have constantly had me laughing, we had a common connection. He was best friends with my ex-boyfriend’s cousin. Though he did reach out after the date, he never asked me out again. I’m glad he didn’t, because I probably would have gone.

4. The Musical Nurse: He was extremely thoughtful and compassionate. He was reading all of my blogs when I met up with him for a beer and suggested I try his beer before ordering (It’s fine, he was drinking the beer too). We talked about life, traveling, friendships, relationships, our professions, and the band he was in. While I enjoyed his company, I’m not sure we clicked romantically. Yet, I agreed to see him again later that week. Sadly, I had to cancel our next plans and neither of us ever got around to planning something else. I really hope he finds a great woman, but it’s unlikely that I’m that woman.

5. The Entrepreneur: When it came time to meet this guy, I was both nervous and excited. Not only did he have a great job, but he did real estate on the side, AND he had just bought his own house that he was remodeling. We met for coffee and then (he) talked so long that we both got hungry and ended up going for sushi. Five hours later, I was interested in getting to know him more. He texted immediately after our date, but throughout the week as I was on a business trip, the texts became sparse and less interested. I reached out to ask about his week when I returned home and didn’t receive a response for three weeks. Apparently, due to some health issues, he didn’t feel like he’d be able to give me the life I deserved and didn’t want to hold me back. While I appreciated him breaking up with me after one date, I didn’t appreciate not being responded to for three weeks or him thinking I was ready for marriage.

6. The Valentine: On Valentine’s Day, a guy who I’d been talking to was hinting at seeing me. So I asked if he wanted to get together that night since I had plans for the rest of the week. We met for coffee, because he didn’t drink. This man was extremely attractive. While I’m generally pretty conservative, I was having extremely inappropriate thoughts about him. Stereotypically speaking, the conversation just wasn’t there. We spent two hours basically talking about the gym and working out. He did light up when he spoke about his daughter, but otherwise it was like pulling teeth. He too texted right after, but we never made plans again. The attraction was there, but nothing else.

7. The Drunken Dad: Leading up to the date, I was actually pretty interested in his laid back approach. He was more suggestive than pushy. We met at a swanky hotel bar/restaurant which he later apologized for taking me to knowing I travel so much. The date started off great and I was really enjoying his company. He had been married previously, lived in and traveled to other states, and had a young daughter. There was great conversation, chemistry, and mutual interest until he had one too many drinks. I prefer first dates to be pretty casual and short (disregard the length of the date of the entrepreneur because that was a Sunday). This guy was not letting me leave. He wanted me to get dinner with him and suggested I reconsider my no kissing on the first date rule. Though he started to irritate me, I waited until he paid so we could walk out together. I figured he was embarrassed of his aggressive behavior when he didn’t text, until he texted a week and a half later telling me we both dropped the ball without an apology.

8. My Favorite Number: From the moment this guy started messaging me, I was instantly interested. He was exactly “my type.”Tall, witty, passionate about both his profession and his health, in to sports, and so handsome. I didn’t stand a chance. He was the first of the dates that I was completely anxious about meeting. The nerves were so real that I arrived 30 minutes early (this NEVER happens. I’m either right on time or late). He got there 15 minutes early and the conversation flowed easily. We spent part of the date laughing at the other obvious first date next to us. He paid, (when the server asked the date next to us how they wanted their check, both my date and myself had a collective sigh of relief when the guy paid it) walked me to my car, and I drove him to his. He immediately messaged me witty banter that went back and forth that night and then nothing. I followed up a few days later giving him my number with no pressure to it. Sadly, he never responded and unmatched me.

After going on these 8 individual dates, what I expected to happen finally happened. I’d become so distracted with these men that I almost forgot how upset I was about being “dumped”. The other thing that ended up happening was I had become so irritated about going on so many meaningless dates (sorry to any of the fellas that I went out with) that I finally decided to quit using all dating apps. While I enjoyed most of the dates, it’s like interviewing for a job that you don’t end up getting. For the most part, each of the guys were polite and they all paid for me. However, there was a lack of something from one or the other of us in each scenario.

This piece is simply meant to elicit a laugh. But in all seriousness, I know what I want out of life and the type of person I hope to share it with (Hey Favorite Number, I’m still single!). Despite constantly feeling like I am running out of time, I really can’t afford to waste any more time searching for who I am meant to be with. Just because I am refusing to put in any effort in the search, doesn’t mean that my fingers aren’t crossed that the powers that be will have him show up sooner rather than later. TC mark

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