4 Stories For Those Frustrated With Dating

frustrated with dating

By Jackie Pilossoph, Founder, Divorced Girl Smiling, the place to find trusted, vetted divorce professionals, a podcast, website and mobile app.

I have never met someone who enjoys dating all the time. I always found dating to be like somewhat of a roller coaster. First dates can feel awkward, and can result in a painfully long dinner with Mr. or Ms. Definitely Not Right. Then there’s the disappointment of not hearing from someone with whom you were sure you hit it off. As you can see, I have some experience with dating, specifically being frustrated with dating.


All that said, dating can be wonderful.  You meet one person with whom the sparks are flying and that makes it all worth it. Dating is like a drug. No matter how many duds you meet, single people looking for that love high keep going back for more. Why? Hope. We’re willing to put up with all the jerks, liars, cheaters, womanizers and weirdos because deep down we know we only need that one awesome connection—that perfect person who will make all the less-than-perfect experiences worth it. In other words, if you don’t play, you can’t win, which is why we put up with being frustrated with dating.

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I didn’t get married until I was 35, and seven years after that I got divorced and began dating again until I met my significant other at 49. So, you do the math. All in all, I’d say I played the dating game for at least 25 years of my life.


These days, my love life is picture perfect. But, it took a long time to get here. The journey included a broken heart (multiple times), along with a rollercoaster ride of frustration, excitement, shock, disappointment, and a weariness that made me want to give up and accept the fact that meeting the one just wasn’t in the cards for me.


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A reader, who is a single mom with three kids is frustrated with dating:


I am worried that I will always be alone and never be in a relationship ever again. Dating is exhausting.

The best way for me to offer advice for frustrated with dating  is to share four of my dating stories. I hope that will make even the most frustrated dater realize these things: dating is a numbers game, you can’t take anything personal, and like I did, you will survive.


1. Honey we’re out of milk.


Shortly after I got divorced, I met a guy at a high school reunion, who I didn’t know in high school. We hit it off and he decided to come to Chicago to visit friends and to see me. We went out a couple of nights and he seemed extremely interested. I didn’t really feel connected in a romantic way, but he seemed like such a sweet guy.

The day he was leaving, I drove him to the airport, and just before he got out of the car, he asked if he could see me again. I wasn’t sure how I was going to let him down. I felt terrible. All of a sudden, he got a text on his phone, which was in his hand and in my full view. It read, “Honey, we’re out of milk. Do you want me to pick some up before you get home?” Guilt turned to shock and disgust. I think my jaw was on the ground the whole time I was driving home on 294.


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2. I feel like I should be in love with you by now and I’m just not.

Before I was married, I met a man through mutual friends. He wasn’t particularly attractive, but he seemed kind and safe, and I talked myself into liking him. We dated for about three months, but then he began acting distant. He didn’t call as much, and was sort of rude to me on a double date with our friends. I asked him, “What’s wrong?” He answered, “I feel like I should be in love with you by now and I’m just not.” Ouch. That killed me. What I realized was, if you’re settling, the person can tell.

3. By the way, I cheated on you.

The end of a long-term relationship is never easy for either person. But in this case, the person was so hurt, that he decided to try to hurt me. As we tried to maintain a friendship, we were talking on the phone one day, and he blurted out, “Just so you know, I cheated on you the whole first year we were together.” I felt nausea followed by rage followed by sadness. Here’s the positive: I had suspected it for years, so finding out he really did cheat made me feel validated, like I wasn’t that crazy, insecure girlfriend. Still, it killed me.


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4. I’m just not that into you.

He’d call. We’d go out. We would kiss. And then I would wait for a text from him that wouldn’t come for days, sometimes weeks. This pattern went on for almost a year. I was trying so hard to get this guy to fall in love with me. I felt frustrated, disappointed, and angry. Getting mixed signals from someone is awful and it’s terrible for a person’s wellbeing and self-esteem. I should have dumped the guy the first time I didn’t hear from him, but I didn’t. I kept hoping he would change. My advice: if a pattern is toxic, so is the person. Run, don’t walk away from the relationship.


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Like me, most people who have dated have a few memorable stories. They might be painful to recall, but think of it this way. Every date and every relationship has some value, regardless of whether or not you walk away hurt. You might not even realize what you gained from an experience until much later.


I think dating makes people stronger and more interesting, and with every date, you learn more about yourself and what you want. In other words, maybe bad dating stories aren’t such a bad thing. The exhaustion of dating can lead to the big payoff: the person you love so deeply, that you feel like all those bad dates were worth it.

Like this article? Check out “There are no Buts in a Healthy Relationship”

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    Divorced Girl Smiling welcome video
    Jackie Pilossoph

    Editor-in-chief: Jackie Pilossoph

    Jackie Pilossoph is the Founder of Divorced Girl Smiling, the media company that connects people facing with divorce to trusted, vetted divorce professionals. Pilossoph is a former NBC affiliate television journalist and Chicago Tribune/Pioneer Press features reporter. Her syndicated column, Love Essentially was published in the Chicago Tribune/Pioneer Press and Tribune owned publications for 7 1/2 years. Pilossoph holds a Masters degree in journalism from Boston University. Learn more at: DivorcedGirlSmiling.com

    One Response to “4 Stories For Those Frustrated With Dating”

    1. Dor

      Your love life is picture perfect.
      That’s great, l but perfect doesn’t exist.
      I guess u learn something from every date.


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