Posted in:
May 4, 2008 12:00 AM by Rich Santos | COMMENTS
I’ve decided to give you a
depository where you can vent your bad date stories. So let me get the ball
rolling. Here are two terrible
ones from the dating files from two of my friends:
Margaret
You all remember my dear
Southern friend Margaret (the one who went out with the guy with the hairy
back). She is one of my greatest
sources for terrible date stories. One of her most harrowing dates occurred at her Debutante Dinner. Yes, you read that correctly.
Margaret’s Debutante
Dinner was a gala event. Even her
87-year-old grandmother made it, something that impressed the entire
family. Her on-and-off boyfriend
at the time, Jake, “invited himself” to be her date, promising that he’d
behave—despite his history of reckless behavior on dates.
Jake's promise evaporated faster than a gasoline puddle in the sun.
READ MORE 
Posted in:
May 4, 2008 12:00 AM by Rich Santos | COMMENTS
As far as “attractive
adjectives” go, I usually get “cute” instead of “hot”. My friends and I have decided that some
people are “cute”, some are “hot”, and some are “sexy”. After some thought, I
decided to define each word, complete with celebrity examples (yes, I even
include guys—I’m a good sport), and occupations.
Cute
Unlike “hot” and “sexy”,
people can morph in and out of cute. For example, someone can grow on you and eventually become cute. When I
dated Other Emily, she thought my Neanderthal way of holding a fork was “cute”. But, in her breakup letter that
shredded my very being, she said that I was a “ignorant (learn how to use
utensils) bastard”. Perhaps the
most revealing anecdote that supports the versatility of the word “cute” is my
sister’s statement from when she encountered a giant roach in her old
apartment:
“I mean I tried to
convince myself it was cute but I just couldn’t.”
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Posted in:
April 29, 2008 12:00 AM by Rich Santos | COMMENTS
I’ve learned that girls
notice what you’re wearing, especially when you’re not wearing much. One time I was making out with a girl
in my boxers and socks—well they were my “old man black work socks” that I had
worn with my business casual work outfit. I was entirely too lazy to take these socks off and proceeded to make
out with the girl with no shirt on, but in boxers and the work socks—the look
popularized by the grandfather in Sixteen Candles when Sam first sees him in the movie. After a few minutes, the girl I was
with said: “can you please take those socks off, it’s just a terrible look.” I really wasn’t that into her, so I
refused. We never spoke again
after that night.
With their snug fit, boxer
briefs exist comfortably with any pants. But it’s sad that I’m too fat to wear
them. So, I’ve continued to wear
the kind of underwear I’ve always worn: boxer shorts. But is my allegiance to boxer shorts making me look un-sexy
when I have amorous moments in the bedroom?
READ MORE
Posted in:
April 27, 2008 12:00 AM by Rich Santos | COMMENTS
The other day I
unwittingly answered the ever-popular question as to why guys disappear after
seeming so interested. I’ve been the victim of girls pulling strange
disappearing acts on me as well. So, I stepped back and looked at it on a human level and tried to
simplify it as much as possible.
Lately, I’ve been on a
string of dates that have been OK, but nothing special. My friends (more and more of which are
getting engaged or more serious with their significant others) have been asking
me to assess every date, since the spotlight is focusing more on me these
days. After getting berated by
statements such as: “you’re too picky,” “you’re just making excuses to stay
single,” “stop being so critical,” I finally came out with:
“I’m not going to be into
anyone or anything that I don’t want to go out of my way for.”
After I finally said it,
the light bulb went on in my head. Yeah, I’m picky—there’s not much I will go out of my way for. But how many people really go out of
their way for many things? And how
many unions between two people occur out of convenience: “it was just so easy—it
was right”, versus “I realized when I would do anything to get to see them,
they were the right one”?
READ MORE
Posted in:
April 27, 2008 12:00 AM by Rich Santos | COMMENTS
I have a lot of friends
who are questioning whether their long distance relationships are worth the
trouble. Ever since I tried it
(even though I was 18 and it was only about an hour’s drive distance), I’ve
sworn I’d never try it again.
I’ve developed a theory on
what makes a strong relationship. It’s called the “Down Time-Crisis Theory”. Take a look, and tell me if you agree with it or
disagree. It is the main reason
why most long distance relationships don’t work.
The Downtime-Crisis Theory
states that no relationship is strong and complete without a sufficient amount
of down time spent together along with crisis situations.
Everyone has fun on big “event”
dates. Let’s say you are
compatible and have a great time together. So, you got out on a lot of big “event dates”: dinners, weddings, Broadway shows,
movies, etc. Who doesn’t enjoy a wonderful meal at a great restaurant? The argument can even be made that a
great dinner or Broadway show makes your companion even more attractive. I mean, an awesome dinner and show
would make even Darth Vader bearable.
READ MORE
Posted in:
April 24, 2008 12:00 AM by Rich Santos | COMMENTS
As another round of
weddings approach this summer, I’m reminded of the time I realized that my
attraction to younger girls was getting awkward. It happened at my friend Cara’s wedding. Cara has the tendency to be a bit high
maintenance. In college I would do
crazy things just to watch her reactions. Due to the nuances of our friendship, Cara felt obliged to warn me not
to do anything stupid during her black tie Manhattan wedding. I couldn’t attend without doing at
least something though. So I
showed up in one of those conductor maestro tuxes with tails.
Seating arrangements at
wedding dinner tables are as intensely scrutinized as seating arrangements in
grade school, or group divisions during field trips. At my table was my accountant roommate Ryan, Cara’s little
sister (Alison) and her friend, both of whom attended Tulane at the time. They were a bit younger than us—let’s
just say that I attended Alison’s Bat Mitzvah when I was in college. It felt
like a successful night, because I was conducting conversation with ease,
appropriate since I was in a maestro tux. Eventually we infiltrated the girls’ hotel room.
READ MORE
Posted in:
April 19, 2008 12:00 AM by Rich Santos | COMMENTS
I
realized that I worry about far more things than I originally thought. So here are some more fears that guys have,
continued from my previous list:
Is
this the end? Is there something better out there?
As we get
deeper and deeper into relationships, there are those checkpoints where we ask
ourselves if we want to keep going. Will
we forfeit our chance to meet someone better? Is this the last girl I’ll ever fall in love with? Seems like depressing things to worry about
if you’re in a relationship, but do we really always end up with someone who is
truly the best person we’ll ever meet and that we are madly in love with?
Did I
say something stupid?
If you’ve
read my other blog entries, you’ve learned that I’ve said a lot of stupid
things. When guys are talking to girls
for the first time, they rely on some tried and tested things to talk about,
along with a hybrid of topics that are based on what’s going on around them at
the time. However, guys wonder if a girl
is just being friendly or if she’s really into what he’s saying. I’m an expert at blurting out stupid things.
Does
she notice me staring?
I’ve
worked very hard to undo my biological tendencies but sometimes I just can’t
help but stare. When I see boobs pushed
up at the top of a shirt, or from a certain angle, I just stare sometimes,
whether it’s a stranger, friend, or romantic interest. I apologize to all women for my occasional
lapses in control.
READ MORE
Posted in:
April 19, 2008 12:00 AM by Rich Santos | COMMENTS
My
Catholic-obsessive-compulsive grandmother had a huge influence on me growing
up. She is part of the reason I’m such a
worry wart. She’s also part of the
reason I have such strange thoughts running through my head all the time. Whenever she sensed me putting a gorgeous
girl on a pedestal, she’d bring me right back down to earth. She’d tell me:
“Rich, if
you ever find yourself getting too wrapped up into a girl—remember, she craps.”
I’ve
tried to find other ways of keeping girls in perspective since then. One of my strategies is to remind myself
that, while they may not worry as much as I do, girls worry about things. So I’ve laid out some things men worry about
so that girls can remind themselves that we worry too. Some you may already know, and some may
surprise you.
READ MORE
Posted in:
April 17, 2008 12:00 AM by Rich Santos | COMMENTS
Sometimes
it’s hard for me to differentiate falling in love with someone versus falling in love with the idea of someone.
My sister once
met a British concert pianist during a business trip. I wish I was clever enough to make this stuff
up, but...
She returned,
ready to break up with her boyfriend of three years, and ready to tour the
world. I figured she was just ready to
get out of her relationship and this impossible dream guy was the excuse she
needed.
But after
a trip to Dewey Beach DE this past weekend, I found a way to relate to what my
sister had gone through.
Sadly, my
version of a “three year relationship” was just a girl that I was trying to
date who was simply having none of it. Around this time, I went to the beach
with my buddies and, at our favorite bar-- The Starboard-- I met this
incredible girl.
READ MORE
Posted in:
April 12, 2008 12:00 AM by Rich Santos | COMMENTS
Here are the rest of the reasons I’ve never enjoyed sex (check out the previous post for the full effect):
4. What If she’s not enjoying it?
I get turned on when the girl is turned on. Sometimes when I’m with a girl I’m worried that she’s not enjoying it or that I’m doing something wrong. Instead of losing myself in the feeling, sometimes I’ll read too much into a girl’s reactions.
“Uh oh, her body twitched when I did that. Man, she probably didn’t like what I just did at all—she’s lost all confidence in me, and she’s going to tell her friends how bad an experience this was.”
Naturally the moment is ruined as soon as those thoughts creep up. If a girl is not having fun or feeling excited when we are together, there’s no reason to be there. This also leads to me not making a move when a girl gets in bed with me—I don’t want to be touch-feely guy. I’m always worried that if I make a move, I’ll offend a girl or overstep my boundaries.
READ MORE
Posted in:
April 11, 2008 12:00 AM by Rich Santos | COMMENTS
I don’t know how many guys you’ve heard say this but: I’ve never enjoyed sex. I don’t know how many times, exactly, that I’ve had sex. I have been with 9 partners, three of which I’d consider “girlfriends”. Five partners were “one night stands”, and one was a good friend that I had previously dated when we were too young to have sex.
Over the next couple of days, let’s try to figure out why I have never enjoyed sex. I realize it’s not a normal thing for a male to say, but it’s the truth. Here are the reasons I’ve come up with on my own and with friends over why I’ve never enjoyed sex:
READ MORE
Posted in:
April 10, 2008 12:00 AM by Rich Santos | COMMENTS
Not making enough of an effort to find the special girl has been an issue for me. I knew I had a
problem the time my two friends-- Al and Justin-- and I visited my sister at
Newport Beach, RI.
We were summoned to RI under my sister’s headline of: “You
guys won’t believe this place: The Atlantic Beach Club (ABC). My friends and I will be partying there
outside all day—there will be tons of girls there”.
Naturally, my buddies and I headed up to RI with high
hopes. There was a great venue
(beach towns are always good venues), and my sister (who went to Boston
College) was a total in. After all
these years of bothering my sister to help us meet her friends, we were finally
going to immerse ourselves into the scene under the sun in a great bar.
This is where the mistakes began.
READ MORE
Posted in:
April 6, 2008 12:00 AM by Rich Santos | COMMENTS
I’ve been walking around town thinking of what I want in a girl (not in terms of physical appearance). I ended up putting together a little list of what girls can do to attract me, figuring out how each would help in a situation such as running out of gas together. Maybe most people's true colors and character come out in times of crisis. Running out of gas together can be totally romantic...or it can just suck. It is what you make of it. Keep these four things in mind—I’ve talked to other guys who agree on all these points:
1. Smile
Everyone likes a positive person. I’ve had too many girlfriends and dates that seem to be jaded and bitter for whatever reason (maybe because they are hanging out with me). A girl who smiles a lot is soothing, plus so many girls’ smiles are just so cute. So, if we ran out of gas, maybe all we can do is smile and realize it could be worse.
2. Have a sense of humor, and the ability to laugh at yourself
I hear girls love a sense of humor in guys—not that it has worked for me. Well, we love it too. My sister once told me that I was not going to be happy until I met a girl who made me laugh. At the time I scoffed at her—I was the funny one, and I planned to play that role in any relationship. But these days I long to find a girl who can make me laugh. Plus, there’s nothing cuter than the gorgeous girl who is a total klutz and can make fun of herself. Showing the ability to make fun of stupid TV such as overblown Lifetime movies or late afternoon hungover TNT '80’s flicks is a must. If you can see running out of gas as an adventure (how will we figure our way out of this one) versus an annoyance (you stupid jackass, I told you to fill the tank earlier), then we might have something there. OK, you can say both, just as long as it's still an adventure.
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Posted in:
April 3, 2008 12:00 AM by Rich Santos | COMMENTS
Ever wonder why guys tend to go tearing off without maps up unfamiliar exit ramps, start putting together things without looking at the manual, and generally have the inability to follow instruction? We are victims of the g-spot. We don’t know any better than to fumble around aimlessly until we accomplish our mission. No other phenomenon demonstrates the vagueness of females better than the female orgasm. I think I’ve given a girl an orgasm before? It’s that same feeling as I used to have after completing a huge math problem: I’d turn to the back for the answer and I was either correct, or way off. But, even when I was correct, I was never sure I was right until I checked the answer…and I could never remember how I even figured out the answer.
It almost feels as if I just lucked out if I give a girl an orgasm: It’s like accidentally opening a secret passageway in an old house by pulling the correct book from the book case. Problem is, even if I’m repeatedly with the same girl, her shelves are lined with similar looking books, which seem to change order…and there’s no guarantee that I’ll ever find that book again to open the secret passageway. Was that even how I did it in the first place?
And what is this g-spot anyway?
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Posted in:
April 1, 2008 12:00 AM by Rich Santos | COMMENTS
I don’t know about you, but I’m reporting suspicious
activity regardless of what the Homeland Security Advisory System states. Whether the threat level is green or red, a bomb is a bomb, and I’m
always going to be on the lookout.
Before disposing of this model altogether, I found a use for
it to outline the stages of a relationship. Under my assessment, I think I’d like to stick to Green this
summer—and maybe move into Blue/Yellow by the Fall. Where do you think you fall on the scale? And, do you have suggestions/additions
to my color level assessments?
Read on for The Relationship Advisory System.
GREEN: Low Risk
of Marriage
This is where most men think they want to be. 3 AM booty calls are the norm. Whoever happens to have cash on them
pays for meals when you hang out. You refer to one another as “friends”. You’re mostly out in groups if you do end up starting the
night out together. You both feel
that there may be someone better out there, but you’re just having fun. There
are no expectations. Going a week
without contact is just as acceptable as being together for 48 straight
hours. Usually Green is short
lived, though gifted couples can stretch it out for months. Sex can be great at green, but
sometimes it is a bit empty.
BLUE: Guarded
Risk of Marriage
Hmmm, this person just won’t go away. The Blue stage is all about more
intense testing. You’re starting
to go on one-on-one dates, taking turns doing what each other likes to do, but
usually pretty casual: dinner, walks, short trips, running errands, attending
parties together, etc. You’re
finding out if you’re compatible at Blue. No more going more than a few days without talking. Blue can be incredibly confusing as you
both wrestle to figure out what the other is thinking and where this thing may
be going. At Blue, you realize
that your companion hooking up with someone else would be mildly
disappointing. However, it may be
the catalyst for a talk: you admit
that it would bother you more than you thought. Whatever the catalyst may be, you both realize that this
thing is getting more serious. Sex here is getting better—you’re getting
familiar with one another and developing feelings.
READ MORE 
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