Problems with Friends...ish

So my friend and I knew this guy when we were both freshmen. At first things seemed normal and we all had some fun times together. Then he started really crushing on her. In conversation if her name came up, he would just gush about her. But she totally was not into him and she even started dating someone else. He has yet to get over her, though. To this day, three years later, he compares every new girl in his life to her, tries to talk with her frequently, took her out for ice cream and brags about how he took a girl with a boyfriend on a date(even though she emphatically states that it was NOT a date, and even if it was SOOO WHAT??), and even consciously bought the same kind of car as her. She's told him many a time that she is not into him, but he seems stuck on her still. What should she do?

--Wary in Wyoming


Okay. So obviously she should not let him take her for ice cream anymore. With most people, insisting on paying for yourself is enough of a hint that the guy won't try to ask you out anymore...on the other hand, dating someone else is considered a pretty strong negative in most circles. So, clearly, we're dealing with a member of the Terminally Dense Brigade here. So we'll need to be a little more upfront. My recommendations are these:
1. Stop talking to him altogether. The situation has progressed beyond Pretending to Stay Friends.
2. In the event that you absolutely MUST talk to him, e.g. he has your cat by the throat, please refer to 1.
3. When you are near him socially or professionally, try to be as repulsive as possible. Do not cover your mouth when you cough or sneeze. Wipe your nose with your sleeve. Then look intently at the sleeve and say something like, "Whoa, there's one for my collection...Anyone have a vial?"
4. If he actually speaks to you and you choose to ignore 1&2, speak only in CAPS Lock (loud and somewhat angry although not quite a shout), and especially while wearing an almost comically scary Angry Face. Like this:
Him:Hello, Sandra, your new socks are very lovely.
You: HELLO. THE CREATURES LIVING IN YOUR FOOT FUNGUS ARE MAKING A PARTICULARLY OFFENSIVE ODOR TODAY. I'M GOING TO NEED YOU TO STEP AWAY. (Or whatever you choose to say. That's just what I'd say.)
Hopefully this will make him really step off, but if all else fails,
5. Punch him in the nards, or have your boyfriend do it. This is about as direct a "No, Thanks" as can be given, and if it is ineffective, you have no choice but to enlist the legal authorities and have him incarcerated in a high-security plastic prison, a la Magneto, enemy of the X-Men.

Or one final option is always saying, "Listen, Troy, I do not want to date you. I have never wanted to date you, and will never want to date you. I'll see you in hell."
Good luck!

I have a friend who is constantly asking me to do things with (read:for) her. She's my friend and is really going through a rough patch, so I try to help. But more often than not, when the time comes and I send her a text that says I'm coming to get her, she has concocted a ridiculous lie about why she can't make it. I don't want to write her off as a friend, because she doesn't really have anyone else...but I can't let this go on! Suggestions?

--Spineless in Santa Fe


Dear Spineless:

There is really only one obvious solution to this problem, and it is...Very Old Squash. Get some pumpkins left over from Halloween-time. Trust me, they can be found. In the dead of night, dress all in black, go to her house, and *squash* them on her porch with all your might. It won't make her stop blowing you off, but it might make you feel better. It would me.