Reader question #52: More Art of No

Hi Captain Awkward,

Thanks for writing awesome advice. Your blog has become a primary go-to for assessing awkward human interactions!

I’ve been trying to sort out how to handle an online dating situation. I went on a date with a guy a little over a week ago, and while he seemed nice enough at first, further evaluation has led me to believe that he’s a Nice Guy and I don’t have any desire to strike up any kind of friendship or romance with him. The problem is that prior to this assessment, I agreed to maybe having dinner again. He has since written me twice, stating that he really wants to see me again, and soon. I don’t want to “let him down easy” or be completely brutal – but am having a hard time finding the words to say, “Sorry, I was wrong. Let’s not be friends.” I guess one upside is that I’ll be leaving the state in six weeks, so I never intentioned for this to be a long term anything. The downside is that he mentioned the possibility of more job opportunities in the same state and city that I’ll be moving to, so my mind has already raced ahead to worst case stalking scenario. I know that once I let him down, I have no control over how he takes it. At the same time, I don’t want to be cruel or ambiguous about my intent to never see him again.


Dear Petrified:

He’s probably harmless, but trust that bad feeling in your gut that made you sign yourself “Petrified” and think the word “stalking.”

Option 1:  If he only has your dating site email and no other contact info, you can always just never write back and then move away.  Is this the kind of thing where no further contact is good contact?  This wouldn’t be my first recommendation, it is pretty rude, but if you genuinely feel that he will latch on to any further contact, it’s legitimate to protect your own safety.

Option 2:  “Dear ___, I got both of your emails.  I enjoyed meeting you the other night, but I’m afraid I must decline a second date.  I’m so sorry, please take care.  ____.”

Key points:

A cool guy will just say something like “Bummer, I’m sorry to hear it, good luck with your move.” No harm done. An uncool guy will demand explanations so that he can shoot them down or reply with angry stuff.  If you get an “Can I ask why?” reply from him, I recommend that you just not answer.  Ditto for “But you said…” You don’t owe anyone a second date.

Keep it very short. Don’t explain why.  Not his business. He will shoot down your reasons anyway.

Don’t make excuses like “I don’t have time/I’m too busy with the move”  because that’s when stalkers kick into high gear by offering to help you with all your annoying stuff and making it harder for you to disengage.

I can hear Nice Guys reading this, rending their garments and wondering what this poor guy did wrong by wanting a second date.  I don’t know.  I wasn’t there.  Neither were you.  But the letter writer was, and the guy gave her a bad vibe and has already sent two emails asking for a second date presumably without getting a reply.  She doesn’t have to have a reason for not wanting to go out again, beyond “I don’t want to go out again.” She should get the guy out of her life so she doesn’t spend the next six weeks pretending that she enjoys the company of this “new friend” while he gets further invested.

11 thoughts on “Reader question #52: More Art of No

  1. In the case of option 2, I think someone stalky is likely to latch on to the word “enjoyed” in “I enjoyed meeting you…” I’d maybe replace it with “Thank you for dinner…”

  2. And definitely don’t let him know any details about your post-move life, such as phone number, new email, moving date, etc. In my experience, if you get the feeling that someone would become stalky, its for a reason. (gift of fear, etc.)

  3. Also…look, I know Captain Awkward’s feelings on this, but silence-as-refusal is a thing. It’s not always clear, and it’s not very nice, but it’s not uncommon in situations like this. A normal guy will at least consider the possibility that you are not emailing him because you want him to go away. If he gets upset about your lack of response, his expectations are unrealistic.

    1. This is a great point. I worry about it with the Clueless Nice Guy Stalker types because they take silence as assent and I don’t want him to “get worried” about her and start checking in at her work and escalating contact. But yeah, just never writing back: It’s a thing.

      1. Oh, totally–and, really, people should get used to establishing boundaries instead of just hoping they’ll stay there by default. Especially with Clueless Nice Guys, since they seem to be laboring under certain relevant misapprehensions vis-a-vis your desire to fuck them.

    2. I do think a normal guy would send two emails before giving up. So hopefully that’s the end of it.

      1. And a normal person who thought he’d made a real connection and is wondering if you’re okay or if something is wrong might even go to email 3 to say “Hey, I don’t want to make it weird, if you need to bail on dinner that’s cool, take care.” Cool people give other cool people the socially convenient “out.”

  4. Good news: It all worked out in the end. I told him I didn’t want to see him again, no reason given, but best of luck out there. He responded by insulting me twice (because I “jumped into” meeting him too soon, he thought I was a person “worth knowing”). I then went on to explain my perceived pros and cons of my approach to dating, and acknowledged that I should have said something sooner. He wrote back and wasn’t nasty about it, and so the situation is resolved.

    Part of my approach to online dating is to only contact the other person through the site, until I’ve met them and decide that I want to exchange emails or digits or whatever. I definitely feel more secure by limiting contact options.

    I think that sometimes I jump ahead to “worst case scenario” because of bad relationships in the past. I’m still really new to online dating and while it’s getting easier, in the back of my mind every guy could still be Schrodinger’s Rapist, or turn into angry guy. Still, it’s good to have the skills to be able to say no, even when it’s hard or a bit scary.


    1. Wow, how could you get a catch like that get away?

      Bravo, your instincts that he was horrible were right on and you did exactly the right thing. Good luck with your move and your new life, etc. Don’t be a stranger.

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