Dating in my late 30s
Step back and look at this from his perspective. If I am introduced to a woman at a party or at a bar through common friends, it takes only a couple of questions before we are discussing what we do for a living.
Dating was simpler then, even though at the time I felt like the world was being altered around every decision I made. Take, for instance, your co-worker crush. Not everyone is equipped to do that.
There was something about that sense of discovery in life and mutual fear of the unknown that served as the best way to connect. Summon every ounce of patience at your disposal as you wade back into this murky and turbulent pool. There's this guy I've been crushing on, we work together, and the other night, I suggested we hang out. Then, just as suddenly, hanging out turns to making out. You might want to try a real date or five with him to figure that out instead of weighing it all on a night out of drinking and buzz-fueled smooching.
While you've been ready to move on for some time, they might not know that, or believe that. In fact, what she used to see as your strengths have now become weaknesses. In fact, they might assume you're still processing the past, or in rambunctious rebound mode. You need to turn your approach inside-out.
And those who are already know most of this. And then making out turns into getting the heck out. Not dating after so many years will be even harder. This speaks to your confidence, which will be your biggest internal support as you re-enter the mysterious kingdom of the single and available. The emphasis was more on being unphased by the impending pressures and less on looking like you had a perfect road map.
The point is that confidence comes from knowing where you are and what you bring to the table, and owning it. Maybe he is into you, maybe he isn't. The problem is I just don't know how to go about it.
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