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A tale of two dates

It was the worst of times, it was the worst of times

Those of you who used to closely follow my dating exploits and adventures will be thrilled to know I've reentered the dating game. Well, I've had two dates in 2024 which is likely more than all of 2023 (by choice), but it's a start. And perhaps an end. But I digress. Let's talk about both of these eligible bachelors. Bachelor #1...


Apparently Dry January is a sliding scale

Date #1 seemed great. Met on the apps, texted a bunch. Was complimentary and attentive. Asked questions and had a genuine interest in me. I mentioned I was doing dry January and he said after a trip overseas he was detoxing/doing the same for the remainder of the month. We met after an event for a quick drink in the city.

I decided I'd have one drink (drizzle or misting January?) and that was it and apparently he was easily persuaded. He then proceeded to have four IPAs. In about 2 hours. These are approximately 10% alcohol for those keeping score and also doesn't quite align with his goal to me of detoxing. Maybe he meant retoxing?! Needless to say, he got a little drunk (this is a grown-ass adult in his 50s). The intoxication was enough to be noticeable.

I'm at the age and point in my life where I no longer make excuses for people and to me this showed that he doesn't mean what he says and I can't trust his word. Who was the real "John" (not his real name)? I'll never know but I have a strong suspicion it's someone with a drinking problem. Now, onto Bachlelor #2...



Ever been in an elevator or ran into someone who shares their entire intimate life story, unasked, in 1 minute? That was Bachelor #2.

He and I also had a great pre-meet rapport. He was also quite engaging, asked questions, seemed very excited to meet me and checked a lot of boxes. He doesn't drink at all and again, still January, so we met for dinner since neither of us was imbibing (and we didn't). I don't normally do a food-based first date, but I figured at the very least we'd get along and have a good time.

Everything was going great until about an hour into the date when he mentioned that he's currently estranged from his children (who we discussed a lot) because he committed ongoing illegal activity at his last job. Ummmm....

I won't get into the details but needless to say, how do you respond to something like that? In fairness to him, there's likely no good time to bring this up and I do respect his radical candor. But on the other hand, it's a lot to dump on someone who doesn't know you. My guess was this was all part of his therapy and recovery, but it got very...


No one gets a rose

I talk a lot about how I don't like the phrase "Bring your whole self to work" because I don't think anyone can or should. I think there are things about us that are private or perhaps private to a small group and not really anything you should share with the wider world. No one needs to know everything. That's what loved ones and partners are for. Or inner thoughts. Or therapists. Or your journal.

In the case of these two dates, Bachelor #1 seemed uncomfortable with who he is and probably needs Personality Brand. He needs to be able to be more himself and not go overboard because he's holding himself back all the time (nothing says discomfort like the need to drink too much). While Bachelor #2 needs the boundaries of Personality Brand. It's not about sharing everything. It's about sharing the parts of yourself needed to make a connection. And like all connections, these things develop over time. And with comfort and safety, then you reveal more. It's never all or nothing. Or immediate.

So when you think about how and what of your own personality to share with others, let this be a reminder that you can start small. But always be truthful.

That you can slow roll your reveals when you feel comfortable. But not overshare immediately.

That the right people, environment, organization and clients will accept you for who you are and not ask you to hold back or unleash the Kraken.

And just like dating, it could take a while to find that fit. But the more honest and genuine you are from the outset, the more likely you are to set yourself up for success and find your ideal match.


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Job hunting?

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