View from the Male Room: The Latest Dating Mistake Revealed!


I have the great fortune of coaching men, and as a result I get an inside look at some of the “ugh” type mistakes (and I mean, the mistakes that make my male clients go, “ugh”). In fact, if I were to interview these women, I’m quite sure they would have NO idea how the men had responded to their behaviors (based on the way in which they “follow-up” with these men and continue to pursue their “target.”)

While there are the usual mistakes women make such as texting immediately after the date to “check on him,” to make sure he arrived home safely, asking him out after the first date,” and inviting him to a party to meet your friends during week ONE of the courting process, the new trend in dating mistakes I am seeing now is what I call: ”The Upsell”

What exactly is The Upsell? It’s a mistake that looks something like this: A guy who have just met (online, at the coffee shop or at an art even) asks you to meet for coffee or go for a walk on the hiking trail on Saturday afternoon. You respond this way, “I have plans on Saturday afternoon, how ’bout dinner Saturday night?” Ergo, “The Upsell.”

You have taken an invite for something low-key and casual and tried to up it to a date with higher stakes. The truth is that the meet date (coffee, hike) is the best way to get to know him, without putting pressure on the situation. In fact, many men and women might agree, the official “dinner date” can be one of the most ineffective and awkward get to know each other situations as their are menu prices involved, chewing food, and choosing how much alcohol (if any) to drink. This scenario invites pressure!

The bottom line is this Dignity Daters: If a man asks you for a date, ensure that even if you are not available at that time, you maintain the feminine role by choosing NOT to suggest another date alternative. In fact, tell him you are busy and give another time you are free during the same hour of the day. (e.g., he asks you for morning coffee Saturday, you suggest Sunday morning.)

Trust me, the upsell makes a man wince (and I have seen these winces first-hand, and they are no less powerful even when it’s thought off in the telling of a story.) If this resonates for you Dignity Dater, there is a chance this masculine dating energy can unconsciously be impacting your success more than you could imagine. 

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