Breaking up with someone you meet conventionally is pretty easy. I mean, it’s not, it’s gut-wrenchingly awful, but at least you know how to do it. You meet them in person, apologize for having to do this, then brace yourself for the angry crying, or the disappointed crying, or perhaps a potpourri. How do you tell someone you met online that you don’t want to see them anymore is a touch more complicated. Here’s a question from Margaret, a loyal reader new to the world of Internet dating…
I’ve gone on a few dates with guys who are nice enough, easy to talk to, but I don’t want to rip their clothes off. How and when do I call it quits? Where is that nebulous line between “giving them a chance” and “leading them on?” And what is the text that says “hey you’re nice and thanks for all the free booze but I’m just not attracted to you” without saying it in so many words? When do you have to call instead of text? Should you ever say “Let’s hang out as friends sometime” or are you both just kidding yourselves? Help!
No so fast! To read my answer to this and many other vexing internet dating problems, buy my new book Not a Match: My True Tales of Online Dating Disasters. Makes a great gift for birthdays, anniversaires, and weird funerals!
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It's Not a Match.com 
If asked on a second date following a “he was nice, but I have no desire to ever see this person naked” kind of date, this is my “go to” response: “I enjoyed our date and think you’re a great guy, but I just didn’t feel enough chemistry to go on a second. Thank you though, and I wish you the best of luck with everything.”
I had a guy completely blow me off and disappear after 5 dates recently, and I vowed I wouldn’t do that to guys I date, even if only one date. It is just a crappy thing to do, to leave someone hanging and wondering. So, I recently sent a “breakup” text to someone I had been on two dates with. (We had not spoken on phone, only text, so I figured was appropriate to send text.) He asked me out for another date in text and I responded with “this is hard for me to say, but I don’t feel the necessary connection to continue to move things forward. I’m sorry”. He responded “ok, thanks”, then I responded “I really do think you are a great person and thank you for the chance to get to know you”. He then said some really nice things about me. It ended very positively and I felt like I handled it like an adult (not like the cowardly guy who didn’t have guts to say something similar to me.) I think it is much better to be mature and have the integrity to just tell someone kindly that you won’t be pursuing things. I think most people will appreciate it and I think it is good “dating karma”, which we all can use a little bit of!
Oh, if only date #61 read this post -he’d fall into the post-nudity break up situation. Thank you for a being a man about dating. You are a man among boys.
Nine dates, post-nudity, allows you to drive across town to tell you in person that he’s interested in someone else? Beat him with a stick and wish him best of luck.
Okay, I have a question for Margaret/B/Oprah/Jesus/Anyone else who wants to chime in,
How do you end up on a 2nd, or gasp, 3rd date, with someone you’re not physically attracted to? I mean I’m far from shallow, but are you guys expecting them to somehow turn you on with their personality despite a lack of physical attraction? That seems like a losing proposition…
Also, B’s typo of “some” instead of “something” is cracking me up…
“I’m sure you’ll find some great soon enough” makes it sound like you’re telling them you’re sure they’ll find some great penis/vagina/ass soon enough…
it’s a far less valuable cut and paste with typos. One day I’ll get them all. Maybe.
I can see ending up on 2nd date with some you realize you’re not attracted to, but a third, no. Sometimes attraction develops and you want to see if it might develop on a second meeting. But hoping for that on a third date is hoping a whole lot.
After reading this, I realized that I may have screwed this up before. The last girl I met online resulted in us “dating” for a few months. I put dating in quotes, because she never contacted me first, ever. Arranging dates or just saying, “hi” was always on me. We typically went out/hung out at least once a week. She met my friends; I never met a single one of hers. Once nudity was introduced to our “relationship,” she still would never contact me first. I let this go on for a few weeks and kept feeling more and more like I was her guy on the side. After our last time hanging out, which was an odd and frustrating experience, I decided that it was on her to continue whatever we were doing. So, I didn’t call her and she never called me either. Do you think I messed up? Should I have called her and ended things?
Considering the specific nature of your relationship– that you were the one doing all the contacting and she kinda sounds Just Not That Into You– I think you’re off the hook. I was in a similar (although not identical) situation with a guy once, and after our last time hanging out, which was an odd and frustrating experience, I decided that the next time he tried to initiate a hangout I’d give him a call to officially break it off. And, apparently he agreed that it had been odd and frustrating, and he never called or texted– so neither did I. Sometimes it’s just mutual. But our blogger may disagree.
John – definitely not on you and you did not end things. If you’re the one making the moves 100% of the time, you gotta just face the fact that she’s just not that into you. You sound like you’re a great guy, and in your description it sounds like you may have been her guy on the side. I’d stop worrying about her and move on, as to calling and ending things? You didn’t mess up, she was just never into it.
You couldn’t have picked a better picture to put at the top of this article… Dawson… Priceless.