Okay, so my best friend (male) has been having a REALLY bad dating life for the past few months. Since August (when his last serious girlfriend dumped him, he’s been on like 28 dates, and i think less than 5 of them even got second dates. He’s scared of relationships, he’s scared of girls, he’s scared of love. He’s an emotional wreck.
So Valentine’s Day is around the corner. This’ll be the first year he’ll be single since practically middle school, and without someone to spend the night with. Even 2 years ago, he had me to snuggle and eat popcorn with as we watched lame romance movies. We were single together.
Given his recent choices and options, I’m assuming he’ll be alone on V-Day, and knowing him, he’ll be miserable. I need something to cheer him up, to make him smile, and enjoy the day regardless. I also need something I can do from across the country, because I don’t live there anymore. I really care about him, and I hate to see him hurting.
Any ideas?
You could send a “pick me up” bouquet from FTD or Flowers.com.
A phone call is always nice and to add to that a nice e-mail with a personalized message about how much you are thinking of him.
I am not a big one for Valentine’s day so I prefer just a card with a few valentine candies inside. For me, it reminds me of elementary school and always lifts my spirits.
Then there is always the “hire him an escort for the night” idea, but we won’t go there. 
Send him a bottle of whiskey and a John Lee Hooker CD. If he’s gonna wallow, he should do it *right/i].
BJ
Did I say that out loud?
Think of when you two first met or something you did together soon after and then get a thoughtful little gift that reminds you of that. Then it’ll have memories that’ll make him smile.
Kitty
LOL, when we first met, he was going out with my best friend. She made me talk to him online one night, find out his opinion on something or another (it was high school, lol, we were allowed to be immature!, so we started a conversation. And we’ve talked pretty much everyday since then. That was over 2 years ago, and I love him more than ever. And BTW, the chick that dumped him in August was my best friend, so I doubt he’d like to have memories of that :)They never talk anymore, me and her never talk anymore, but me and him have stayed friends regardless. It’s a weird, weird world we live in.
Thans for the ideas though 
Send him a prescription for a powerful tranquilizer so he can spend all of Valentine’s Day in a deep, deep stupor.
You should take him out to dinner where the two of you can quietly make fun of all the people posturing for Valentine’s Day. Don’t make fun of the old couple who is out enjoying their thirtieth Valentine’s Day dinner, but poke fun at the middle aged men with their 20-year old girlfriends who are carrying armfuls of overpriced roses.
Then go hang out in an arcade or play miniature golf or something.
Then go to a completely non-date movie and gorge yourselves on junk food together–throw some at each other for good measure.
Just be goofy and have fun. Treat it like it is a birthday rather than the world’s sappiest holiday!** Just be a good friend to him.
**I happen to like Valentine’s Day! So sue me! I’m for any day where being romantic is encouraged!
Guys like things they can use. Give him a bouquet of tools.
I think this is sweet of you and all, but I just can’t get like too sympathetic for someone who’s been on 28 dates in the past five months. That’s not exactly a social drought. For what it’s worth, I think it’ll be a good character building exercise for him to tough it out on his own.
One of the few nice things about being on my side of 40 is that even if you’re single, you greet the coming and going of Valentine’s Day with immense indifference.
Don’t do a thing. If he’s sad and wallowing, won’t a pity call to say “I figured you’d be all sad an lonely because there is no one in your life who loves you, except me who only loves you as a neutered friend thing, so I thought I’d give you a call/send you a care package” just make it worse?
It’s not a social drought, but it’s also not what he’s looking for. He’s more into commitment, and there’s not much of a chance when he’s not even getting second dates. They meet, go out once, he blows cash on them, he never sees them again. Hell, he’s not even getting goodnight kisses! And as for toughing it out…he handles enough crap that I can’t help him with on his own, the least I can do is cheer him up on Valentine’s Day!!
I wish I could be sympathetic. But for a guy who’s last date was over 6 months ago, and who can’t seem to even get first dates, I’m really not able to muster that kind of sympathy.
So he has to spend one lousy Valentine’s Day alone. Boo hoo. I have NEVER had a girlfriend or even a date for VD in my 29 years. My VD gift will probably be from my mom (again).
He broke up with a long term relationship. He’s only a couple years out of high school. It’s okay for him to be struggling with that. If he’s scared of relationships, of women, and of love, then he probably doesn’t need to be trying to date right now. I would suggest that he needs to quit worrying about impressing the women and work on himself. (This from a major low self esteem case.) He feels rejected because of the break-up, he needs to work on being himself without his girlfriend.
Sorry to sound so bitter, but 28 dates since August is hardly a drought, and if he’s not getting to second dates, then maybe he should evaluate who he’s asking out and why. You said he’s looking for commitment rather than just social dating, random match ups. Then I suggest he needs to evaluate his potential dates and see what they have in common/get to know them first. Oh wait, I’m told that’s what dates are for. And don’t even get me started on good-night kisses.
As for being alone on the holiday, these things happen. Get over it.
I wish I could be sympathetic. But for a guy who’s last date was over 6 months ago, and who can’t seem to even get first dates, I’m really not able to muster that kind of sympathy.
So he has to spend one lousy Valentine’s Day alone. Boo hoo. I have NEVER had a girlfriend or even a date for VD in my 29 years. My VD gift will probably be from my mom (again).
He broke up with a long term relationship. He’s only a couple years out of high school. It’s okay for him to be struggling with that. If he’s scared of relationships, of women, and of love, then he probably doesn’t need to be trying to date right now. I would suggest that he needs to quit worrying about impressing the women and work on himself. (This from a major low self esteem case.) He feels rejected because of the break-up, he needs to work on being himself without his girlfriend.
Sorry to sound so bitter, but 28 dates since August is hardly a drought, and if he’s not getting to second dates, then maybe he should evaluate who he’s asking out and why. You said he’s looking for commitment rather than just social dating, random match ups. Then I suggest he needs to evaluate his potential dates and see what they have in common/get to know them first. Oh wait, I’m told that’s what dates are for. And don’t even get me started on good-night kisses.
As for being alone on the holiday, these things happen. Get over it.
Or a bottle of whiskey and a hooker. I know I’d appreciate it.
And so my failure to close my vB code has now claimed an innocent. The humanity!