In the Game of Love, Is the Risk Worth the Reward?

The Magic 8 Ball says…

Robot with a broken heart

I met a guy at the beginning of 2019. It was right after another guy I was seeing abruptly called it off. (And by “right after” I mean the next day, because keeping it moving is the only way to survive dating in 2019.)

On paper, this guy — let’s call him Anthony — is nothing like who I would have described five months ago as “my ideal man”:

He is over forty. ❌

He is divorced. ❌

He has two kids. ❌

But when dating men in their early 30s who’ve never committed to anything in their lives including adulthood without roommates, you switch things up.

Anthony and I matched on Bumble, the dating app I believe is the least wretched of the bunch. He had two too many car selfies and incorrectly used “to” instead of “too” in his profile, but I looked past my pet peeves because he was cute and his profile was otherwise amusing.

We hit it off on a Friday and, within hours, we had made plans to meet the next afternoon for drinks. We were on the same page about what we wanted out of a relationship (see actual Bumble exchange below).

Saturday rolled around and our schedules didn’t sync up, but we texted heavily for a couple of hours. The conversation flowed naturally. He was a smart-ass (so am I), but also thoughtful, vague enough to be interesting, and confident. Ding! Ding! Ding!

When we finally met that Monday, we both lived up to the other’s expectations, which when it comes to online dating, are very low. Basically, we both had all of our teeth, looked like our profile photos and could engage in interesting conversation for three hours.

After that first night, we began seeing one another about once or twice a week — a schedule dictated by his shared-custody arrangement. This was great for me, because to know me is to know I am always busy doing something. I have varied interests, love spending time with my friends and playing golf with my dad. A couple of days a week is all I have to give to a potential love interest.

Anthony treated me very well. He told me all the nice things: I made him happy; I made him feel loved and fulfilled; every time we were together was something to look forward to; he wanted to do things with me…in the future (btw, anyone want tickets to a comedy show in April?)! I met some of his closest friends. I even fell in love with one of his dogs (the other one is nice, too). We agreed not to date other people. Things with Anthony were different. I cannot explain it any better than that.

This relationship was headed in the right direction — if the right direction was a fork in the road on a NASCAR racetrack ablaze with heartache and tears.

Two months and 11+ dates later, Anthony hit me with the “I’m not ready for a relationship” text. Yes, text. [Editor’s Note: If you have been on more than five dates with someone DO NOT CALL IT OFF VIA TEXT. It is disrespectful.]

Now, I’ve been on the receiving end of the “I’m not ready for a relationship” text several times before. I believe men think it’s the easiest way out of dating someone — it is not. The easiest way out is to say, “I think you’re great, but I just don’t see a future with us.” Direct, truthful, and less painful than the modern day equivalent of “it’s not you, it’s me.” (No one ever believes that.)

Anthony’s text, though, knocked me over like a Kardashian finding out via TMZ that her baby daddy kissed her sister’s friend. I can’t say he was “The One” but he was definitely the one I could see myself with for the foreseeable future (whether that was short- or long-term was TBD). And I believed he felt the same way about me. But this was an overnight about-face.

I won’t share the exact details of the text, but he made sure to reiterate that he wasn’t interested in anyone else and that he really liked me. He said he just wasn’t mentally ready to give 100% to a relationship.

My hot take: He’s just not that into me.




I was hurt (was everything he’d told me about his feelings for me a lie? I don’t think so.), disappointed (I opened my heart up for this shit?!), and sad (am I really that unlovable?).


On it’s face, this is a dumb question. Of course I’m not unlovable. Many people love me, this I know. Some were forced into the endeavor because we share DNA, others came to the conclusion willingly because I give good advice and always have gum and Kleenex.

But falling in love looks so easy on television and in movies. I’m not naive enough to believe that’s how it is in real life, but I am a 36-year-old woman who has never been on the receiving end of non-platonic love. Cold, hard fact. Also a fact? This never bothered me BEFORE I set out on my dating quest.

Here’s a text thread between me and a very good friend of mine after Anthony broke things off:

Admittedly, that is some sad shit. But it is 100% real. I am tired of the hunt, the catch and the release. It takes a toll on my soul because, for me, being emotionally vulnerable is a Herculean task which requires energy, and I don’t have enough energy stored up to keep being let down over and over again. And even if I did have it, I’d rather spend it doing things I love with people who already love me, albeit platonically.

So…will I keep dating “for love” in 2019? Probably not. Should I? Maybe.

The one thing I won’t ever do, however, is not be “ready for a relationship” and pretend otherwise with the men I date. And right now, my heart is not ready, because it is stupidly holding out hope for Anthony.

What do you think? Should I keep up the fight? Let me know in the comments.

4 thoughts on “In the Game of Love, Is the Risk Worth the Reward?”

  1. Hi! I’m Anna’s friend! Only you can determine if you want to keep trying the dating game, though it certainly sounds at the moment like you need to lick your wounds a bit before you get back in it.
    That said, I’ll go to the comedy show with you!

    Liked by 1 person

  2. As my best friend’s now ex-husband used to ironically say every time I told him my dating stories: “dudes are the worst.”
    But I think you should keep at it — maybe give yourself some time. Doing enjoyable things with people who love you sounds amazing, and also not mutually exclusive of getting back on the Bumble train. You’ve got this.

    Liked by 1 person

  3. Hi! One thing I did when I was in my late 20s/early 30s was give up on American men. I just think a lot of them suck and they are really not loyal. Sorry guys, obviously I am not talking about everyone so I hope no one takes offense. Can you work remotely in England or Ireland, or anywhere in Europe? What about South America? Go somewhere where you are exotic and will stand out. I guarantee you will find someone. I have been happily married for 17 years now.

    Liked by 1 person

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