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When I was in middle school (around 14 years old), I was friends with a boy (who was outside of my regular "friend group") and so, some friends of mine decided to hook me up with this person.

I didn't really want to date this person, but I didn't want to hurt him either. So, when he "asked me out" (because my friends were pushing him to), I said "yes", we kissed, then went our ways and spent the next week avoiding each other before formally "breaking up".

All this was a long time ago and I can't fix the past, but I'm still wondering:

How could I have refused to date him while minimizing the hurt feelings and awkwardness in order for us to keep being friends (instead of avoiding each other until the end of the year)?

Notes and clarifications

  • I'm guessing my friend wasn't really comfortable with dating me because he was avoiding me as much as I was

  • There was no date planned, just the "social recognition" that we were "a couple" (so, it's more like he asked me "do you want to form a couple with me?" rather than "do you want to go out with me?").

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You have no obligation to handle it any other way than being assertive. Which means: be honest and straightforward. It's not wrong.

Trying to prolong the outcome by acting like you are interested/trying to be nice will just hurt and frustrate both parties more. If he is the one asking you on a date, he has already made the choice to ask you with the chance of being rejected. All you have to say is "no", and that's it.

You will never be able to live your life on a solid foundation if you try to go the extra mile in not hurting other people's feelings, and I'm referring here to people who are approaching you on their own (like asking you on a date). You have the right to say no, and say it immediately. And that's fine.

If the person is hurt, or offended, it reflects their own lack in maturity. It reflects your own maturity if you handle it straightforward and honestly.

I'm not saying be rude, but be honest and friendly. If they're not your type, then that's the truth.

I've had a similar experience many times before: a friend (she is a woman, and I'm a man) has approached me and showed interest in dating me romantically. I felt like I didn't want to hurt her feelings, and honestly this was because I could see that it would hurt her feelings a lot, so I "played" along and went for it (perhaps thinking that I could learn to like her romantically). After a while she grew more and more attached, and in the end this just caused her to get more hurt as I got more frustrated with the relationship, which I never really was into. If I was honest up front, then she would have been hurt a little by the rejection, but gotten over it much sooner.

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Rejection always hurts, it doesn't matter from who it comes.

That being said, everybody takes it differently and there is not one way to reject someone without hurting them (at least not a definitive rejection).

Speaking from rejecting someone: My experience is that it hurts less, if you tell them that it is not because of them, but because of you. Like you currently don't want a relationship/date etc. Though this leaves room for interpretation for the one being rejected. They might think, that at a later point it would work out better and thus they might never really move on.

That is the least hurtful way in the short run. To really spare them any long time hurt, make a clean cut for them. Bluntly tell them that you are not interested in a relationship/date with them. It will hurt, like rejection always does, but they know it won't happen between you two and then that person is far more likely to move on emotionally.

My opinion for rejection is, being the one rejecting or the one being rejected, make it a clean and obvious cut for the sake of both of you. After this, both can move on and don't hold any false hope.

As for staying friends, it's pretty much the same. It depends on how the other party reacts to rejection. You can always offer to stay friends if you really want to.

For the situation you described a simple

I think we better stay friends.

could have been all you needed. You reject their proposal and tell them at the same time, that you want to stay friends. I would not really recommend this for adults.

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    I am a bit baffled by your suggestion to give an excuse, since you yourself say it only leaves the other party hopeful and will probably bring more hurt later on. Why do you suggest an option that yourself find not good ? I really like the rest of the answer though.
    – MlleMei
    Commented Jul 4, 2019 at 10:58
  • @MlleMei I just reread my answer and couldn't find the part about the exuse. As far as I can tell, my whole answer is about making a clean cut
    – XtremeBaumer
    Commented Jul 4, 2019 at 11:19
  • I'm talking about this part : "My experience is that it hurts less, if you tell them that it is not because of them, but because of you. Like you currently don't want a relationship/date etc."
    – MlleMei
    Commented Jul 4, 2019 at 11:42
  • Its not meant as a suggestion. Its meant to compare the options you have and how they play out in the short/long run. If you think that this point is not conveyed properly, maybe you can edit it?
    – XtremeBaumer
    Commented Jul 4, 2019 at 11:46
  • You do say what might go wrong, and that you prefer a clear break, but you're also not discouraging the first option either. To me, the way you presented things means both options are ok. I would feel different if it read more like "You could do X, but this isn't a good idea because of Y and Z".
    – MlleMei
    Commented Jul 4, 2019 at 11:56

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