It's been foreeever since I posted here, but I thought someone might like to give me some dating advice anyway.
I've been very casually dating this guy that I know through mutual friends for a couple of months, but I'm not really happy about how things are working out and I think it's time to end things. My trouble is that he's out of town right now and the next time we're planning to see each other is at a party with a bunch of people that we both know. I'd like to break up with him before the party, but the chance that I could actually have time to have coffee or lunch or whatnot is very slim. Should I do it on the phone? Just wait until after the party? Would it be too awful if I just say, "no thanks" the next time he texts me to ask me to get together privately?
Thanks for any advice... I almost never date friends, so I haven't had to deal with this type of thing before.
If it's "very casual," I think the phone is your best route. It's the more honest/decent thing to to do, rather than have the farce of seeing him in public at a party, knowing you're going to end it. It sounds like you just don't see a future, not that there's something major to potentially work out, or a lot of logistical things to untangle. Given that, I personally wouldn't even meet for lunch - at the most a drink or coffee, but there's probably not a whole lot to say, and I think just keeping it short & sweet is the easiest on both of you. However, "no thanks" via text may just have the unintended effect of dragging it out further. Plus, for me, ending things by text is a bit tacky, no matter how casual.
Sorry it's not working out, but it sounds like you're making the right move. Good luck!
1. Think through how you'll respond if he tries to resist the 'short and sweet' bit. Hopefully this won't happen - hopefully his response will be along the lines of 'Fine, been nice dating you, see you around', or even 'That's a bummer, but I respect your wishes, see you around'. However, there are some people who make the mistake of trying to argue the other person out of a breakup. If this man is one of those, you may find yourself embroiled in a lot of 'But whyyyyyy? What did I do wrong? Was it that time last week when I said X? I can change! Give me another chance!' which can be difficult to deal with if you're unprepared.
So... the best way to deal with that is to refuse to get drawn into discussion. (That's also a great general rule for dealing with anyone who won't take your first 'no' for an answer, by the way.) Just keep repeating the same short, vague phrase a few times, and, if he still doesn't seem to accept it, finish the conversation.
(Him): 'But whyyyyy?'
(You): 'I just don't feel it's working out.'
(Him): 'But what did I do wrong?'
(You): 'Nothing at all. It's not that kind of problem. It just isn't working out between us.'
(Him): 'No, wait! You can't end it just like that! That isn't fair! We need to talk about this!'
(You): 'I'm sorry you feel that way, and I know this is rough for you if you wanted to continue things, but it just isn't working out, and talking about it more isn't going to help. Take care of yourself. Bye.' (Hang up.)
(Repeat as needed if he tries to phone you back/start the conversation again at the party/otherwise restart the 'But whyyyyy?' conversation. If he's making repeated attempts to start it, feel free to skip straight to the final step for subsequent conversations.)
As I say, that script hopefully won't be needed. It's just good to have it to hand if you do need it (with this or a future partner.)
2. On the subject of going for a drink together: The only time to do this is if both of you are happy with the idea of staying friends. If he seems to be extending the invitation as a way to start/prolong something like the above conversation, decline. ('We need some space from each other right now' is a useful phrase there.) If you accept an invitation to have a drink with him thinking it's just going to be a friend thing and he then starts something like the above conversation, cut it off as per the above script (leaving the premises needs to be substituted for hanging up, in that situation).
Good luck, and hopefully none of the above advice will be needed!
If you both think it's very casual, then I'd say a quick phone call would be sufficient. If it's truly very casual, then there's no commitment and thus, it's not much of a break up - more of a heads up really.
If there's any chance at all that he thinks it's more serious than you do, I would meet for a quick drink (probably like coffee, so alcohol can't skew things) and just keep it quick and clear. "It's been fun, but to be honest, it's just not working out for me and I think it's best that we stop seeing each other. Thank you for some fun times and I wish you luck in finding someone with whom you really click and connect." And that's it. I wouldn't get into explaining the whys and hows. Don't answer any questions like if you're seeing someone else (even if the answer is no), or if he could do something to convince you to keep seeing him. Like someone else said, just keep reiterating that it isn't working and you're done, and leave it at that.