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Dating Dilemmas

Over the course of my personal dating history, I’ve been presented with a variety of situations, some of which were really good and some not-so-much.

A good mix of both types have occurred both in the past and as recently as a few weeks ago. Having tried the online method I’ve learned some useful things, but still struggle with others.

Meeting people from online is scary to begin with, as you never really know if the person you’ve been messaging with is anything like those messages in real life, but it gives people like myself who are horrible at in-person interactions a way to “meet” new people with less anxiety over making a good first impression, since you would have had a few conversations beforehand (hopefully).

The biggest hurdle I come across time after time (after filtering out the spam mail and starting the “getting to know you” part through e-mail) is the first date, or as I like to call it, “first meeting.”

Technically, it’s a date, but by telling myself that it is only a “meeting,” it removes some of the anxiety that the word “date” causes me to experience.

When setting up that first face-to-face interaction, I usually like to let the guy do the asking, and make the plans.

It might be a little old-fashioned, but by waiting for them to ask me, it takes away the potential for getting my hopes up and then being rejected if he isn’t interested in dating me. Having them plan the date is also helpful, because while I have a general grasp of things to do/see around the city, there are still a ton of places I’ve never even heard of that could be better/different from my usual haunts.

Once the date is underway, I can usually tell within the first few minutes if I’d be interested in seeing them again, and will gladly continue the date to another drink or dinner.

But, in cases where I’m really not interested, my fear of coming off as rude by ending things early has put me in some awkward situations over the years. Without going into any specifics, I’ll just say that I’ve been dragged along to places where neither the company or the activity were really wanted, and I spent the majority of the time searching for my “out.”

I’m pretty sure most of the time men can tell when a woman isn’t really that interested on that first date, and I’ve been mostly lucky thus far in not having to do the whole confrontational rejection post-date too often.

In the rare case of facing that situation, I come to the next, and biggest hurdle of dating. What is the best method to let someone know that you aren’t interested in further dates (after the first one-three dates)?

Anything more than three dates starts to feel a little relationship-y to me, so ending things from date four and on most likely requires a direct conversation to end things– which is a whole other post I’ll get to someday.

If the person you went on a date with, but aren’t interested in makes contact after the date(s), is it better to reply with a polite rejection, or ignore the message and hope they get the hint?

I’m usually torn when presented with a situation like that, because I like to have details and know what is going on, but at the same time, don’t really like to hear bad news or be rejected. What do you do in that type of situation? And, if you have another method of rejection that works better, I’d love to hear it.



Responses (2)

  1. Are you kidding me? Women never break up in person or face to face says:

    It is better to say you just aren’t interested. I can’t recall any woman I’ve ever gone out on a date with letting me know politely in person they weren’t interested. It’s 95% of the time the cone of silence, or an email or message left the rest of the time. Yeah, that’s classy, IMO.

    Honestly, women are such hypocrites about “breaking up” sensitive to men’s feelings. It makes me barf hearing about how compassionate they are, when not once has it ever been with a personal touch in my extensive experience.

  2. chellykay says:

    I’m in the same boat as you are, having just went on a first date with a guy Sunday night. I kept trying to get away from him at the end of the night and I felt like he was holding me hostage while I was trying to get into my car. I will admit that I don’t want to have a confrontation face-to-face to reject someone. I know it seems immature, but my preferred method is to just break away from further contact. When someone doesn’t respond to your texts; it’s pretty obvious things are over.

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