How do you successfully tell a guy no?

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This happens with woman-to-woman friendship acquaintances, too. Some people do not know they are suffocating a possible relationship before it even gets started because they don’t know they have to take note of whether or not shows of interest have been reciprocated. They are so intent on gaining interest that they forget to leave the other person any room for initiative of their own. This leaves the other person feeling not so much wanted as hunted. The effect is, of course, the opposite of their intention.

That has to do with emotional intelligence, though. It is just as important to be kind to the emotionally unintelligent as to any other lack of intelligence. Just as with, for instance, mechanical intelligence, though, people will also sometimes pretend to be clueless in order to manipulate others into a position they would otherwise not accept. The answer in either case is to say “no,” but kindly. The kindness stays in place, but the firmness escalates as needed.

Dealing with those who become covertly spiteful when refused is another topic. It is worthwhile to ask others what their experiences have been with this person or that, because this kind of spitefulness is not as rare as we might like to hope. The spiteful response to rejection is not something to be unduly afraid of, but it is well worth being aware of the possibility. It does happen.
Given large enough numbers, it’s inevitable that one of these guys is going to turn nasty or dangerous.

I think that the OP is right to be concerned.

Here’s a very good piece on how being socially awkward is not an excuse for bad behavior (warning: non-CAF language):

doctornerdlove.com/2014/03/socially-awkward-isnt-an-excuse/
 
When the first two or three more diplomatic responses have not been taken in the spirit they were meant, then bluntness is required. You don’t ever have to get rude, but you do have to be progressively more blunt. “John, we have been over this, and frankly, I’m done explaining myself! You are a nice person, I’m sure you will make someone a good husband, but I am not going to marry you. If you don’t drop this and take 'no” for an answer, I’m going to have to stop talking to you at all. I don’t want to do that, but you’re not leaving me much choice. I mean it. You won’t get another warning." Then do it.

Now, if you were to say that you were going to cut off social contact if the question were ever raised again after the first time he got up the courage to ask, I’d say that is very rude. You should be more concerned with his feelings and assuring him that he will make a good husband for someone else than you are with the possible unpleasantness of having to say ‘no’ more than once. Otherwise, your answer presumes that this guy finds you so irresistible that he’s going to pursue you no matter what you say. That’s fairly arrogant. Most guys do not want to marry someone who doesn’t prize him as much as he prizes her!

On the second try, if there is one, then you can say, “No. When I said, ‘no’ the first time, I was not being coy. I didn’t not mean ‘try me again later.’ I meant, ‘no, thank you, but no.’ I am flattered that you asked, anyone ought to be flattered that someone like you would want to have her for a wife, but I do not want you to ask again.” If he says, “What if you change your mind?” then you can say, “If I change my mind, I’ll eat humble pie and ask you. Otherwise, consider this my final answer.” On the third try, say: “I meant ‘no’. Period. Otherwise, we’re going to have to put more distance in. You are a nice guy, and I don’t find it pleasant to turn you down. Don’t make me do it again.”
I tried it all. Bluntness, avoiding, talks, explanations, and the topic never got dropped. Even some of my friends started asking me when he was going to get the point and found his behavior bordering on obsessive. So in this case, all I had left was “being rude.” It worked, and no it was not something I would normally have done.

About three or four years later he did write me. He had received mental health assistance with the issue and wanted to know if we could be friends again. I told him no. I felt it was better that we not re-associate again.

It is nice to think that being rude is never necessary, but sometimes, with some people, that is the only option, after all else fails. I had reached the point of wanting to leave the state and changing my name. I had enough and being polite, diplomatic, kind, blunt or firm simply never got the message across.
 
I tried it all. Bluntness, avoiding, talks, explanations, and the topic never got dropped. Even some of my friends started asking me when he was going to get the point and found his behavior bordering on obsessive. So in this case, all I had left was “being rude.” It worked, and no it was not something I would normally have done.

About three or four years later he did write me. He had received mental health assistance with the issue and wanted to know if we could be friends again. I told him no. I felt it was better that we not re-associate again.

It is nice to think that being rude is never necessary, but sometimes, with some people, that is the only option, after all else fails. I had reached the point of wanting to leave the state and changing my name. I had enough and being polite, diplomatic, kind, blunt or firm simply never got the message across.
Yes, it is better to try “blunt to a point that would usually be rude under other circumstances” before you go all the way to the restraining order or carrying a concealed weapon–let alone moving!

I kind of doubt that what you finally had to say was rude under the circumstances. It is not rude to tell someone that they have crossed the boundary of acceptable (let alone polite) behavior so many times that you are no longer going to associate with them. That is enforcing a reasonable consequence for inappropriate behavior towards you, not a rudeness on your part.

When Our Lord overturned the tables of the crooked money-changers who were defiling the Temple with their commerce that preyed upon the poor, that was not rude. It was the money-changers who had crossed the line, not the One who corrected them unequivocally and with authority. The Lord, in his office of authority to correct those who were abusing authority and a position of trust, on other occasions even resorted to name-calling and expressions of contempt. Was he rude? No, He was not. Those He was correcting were that bad, and correcting them in public was His job–that is, the work of a prophet.

I think you were wise to bar him from trying again with you on an intimate relationship. Let him learn what he had to learn from his mistakes with you, and try from scratch with someone else. It is not as if you are the only fish in the sea. You did well to wish him well and bid him luck in his new life without you.
 
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