So here's the deal: Today I went out on my first "real" date in about
3 months and while

everything should have been the perfect setting for "getting to know
someone new" (we went

to a museum - she really wanted to, we walked downtown Chicago, we ate
at a nice little

restaurant and talked a LOT).......at the end of the date, to be
perfectly honest, I didn't

feel anything.

It's really weird because in the past (and quite recently I'd say
within the past six

months) I've been happier with dates that haven't turned out half as
good and in some cases,

were downright terrible (but I seemed to click with the people more).

I was trying some new things though and I'm wondering if maybe I shot
myself in the foot

before the date even began because of my actions. I'll explain - after
I asked the girl out

everything was great. I kept the talking to a minimum and just happily
took her number and

waited a couple days to call. However, because I have been burned in
the past by finding out

weird information on the first, second, or say, fifth dates, I decided
to make up a list of

things I would just casually ask around the same time we talked to set
up a first date. So

after I asked about where and when, I said, "I know this is gonna
sound strange, but I would

really appreciate it if you could answer a few questions up front -
this is just mainly for

me to get a better idea of what I'm getting into and to not be totally
surprised on the

first date...and I'll answer all of these questions back, just so you
don't think it's one

sided." She said it was alright and over the phone (before our first
date), I asked the

following quick questions (replies are noted after):


1) Do you have a boyfriend or fiance or husband or significant other
or anything like that?
[Reply: *Laughs nervously* No, I don't have a boyfriend or anything
like that *then I ask

why she laughed* Well, I just, I dunno, we haven't been together in a
long time and it's

over *then I ask how long it's been over because why would she be
acting weird if something

wasn't there, right?* Well, since I moved here to Chicago two weeks
ago, *thinks a second*

no actually about 5 or 6 months... *then I ask how long they were
together since she seemed

to be going back and forth about this relationship* Well, we were
together for three

years...but he's in rehab in Oklahoma City and I haven't seen him in
months. *then I ask if

she's dated anyone since then in those past few months* *then she
sounds really sad, as if

she knows what I'm thinking as she says* No, not really. *then I'm
like, 'oh, okay,' since I

have nothing left to say.*]

2) Do you have any kids?
[Reply: No. *she laughs, conversations gets away from being depressing*]

3) Do you have any crazy stalker Exes or anything like that?
[Reply: No. *she laughs*]

4) Now don't take this the wrong way, and feel free to answer
truthfully because I'm not

going to like decide on you totally based on this one question...but
you aren't crazy or

have some mental condition or something like that are you?
[Reply: *She laughs* Noooo...I'm not. *I tell her that if she is I'd
rather just tell me now

than have me find out later on because it's something I've ran into
before* No, no, no...I'm

not crazy...]


She asks me back the same questions and I answer, no, no, no, and no,
in that order :)

So we get off the phone and a date (the one that finished up today) is
set up to happen in

three days.

In those three days however, I'm thinking about her reply to the boyfriend/serious 

relationship question a lot. So much so in fact that I almost
completely talk myself out of

going out at all. I mean, if she hasn't dated anyone SINCE the ending
of a 3-year long

relationship, then I'd definitely be the rebound, should things go
anywhere. Is a rebound

ever a good thing? Ever??? Plus, she just got out of a serious
relationship, she definitely

wouldn't want another one this soon should ours develop into
something. Finally, I'm not

convinced she's even done with this ex because of the way she answered
and words she picked.

I mean, I distinctly heard her switch, in mid sentence mind you, from
'two weeks ago' to

five or six months ago' since their relationship had been over. Was it
just a brain fart, or

a Freudian slip? With all that on my mind, I already had serious
doubts about this one.

But, despite that foreknowledge, I decided to try the date anyways. I
figured that maybe I'd

be pleasantly surprised and hit it off with her completely and all my
doubts about her

motives or intentions would be laid to rest.

During that time however, I got a stye in my eye that was pretty
friggin' awful looking (and

painful) but not really enough in my mind to cancel a first date over.
But with the ex-thing

on my mind and being self conscious about my eye that looked like I
got punched in it (it

wasn't that bad looking, but I'm a big person on looking at someone in
the eyes on a date to

see how interested they are in me and it was enough of a problem to
make me NOT want to do

that at all).

During the date however, things were only ever okay at best, never
great, certainly never

spectacular. But overall, the whole date was nice and went smoothly
(we held hands quite

often, grabbed each other by the waste a few times when crossing the
street and in the

museum, etc.). Our conversation never was too heavy on anything and
the banter back and

forth was kinda cute...but I must admit, I didn't find her too
intelligent...and I'm

wondering if that's an issue too.

For example, we're in a dinosaur exhibit and I make a reference to
Jurassic Park, the movie.

She's 27, I'm 23. She has no idea what Jurassic Park is. Never heard
of it...ever. She's

also never seen Seinfeld (a show I love and always reference with
dates and most people in

life) so any references to that in our trip through Chicago was
wasted. Also, she keeps

talking about living in an apartment closer to her school and she
seems so out-of-it when it

comes to pricing and what's even so great over building A or B. It's
like she doesn't have a

grasp on real-world living and she's 4 years older than me! Also,
she's going to college for

Fashion Management which means she likes clothes and actually believes
a job in the fashion

industry is waiting for her (Chicago is a horrible town for fashion
and artsy people because

there are about 10 colleges devoted strictly to those things and
thousands of graduates

every year). Needless to say, as a college educated graphic designer
who worked hard &

luckily found a job in my field in this city, pay a relatively
expensive amount for rent and

living expenses and have been out on my own 100% for about a solid
year now, I found her

views on many things....dumb.

Plus, if she's only now in college, what on Earth has she been doing
since she finished high

school? At dinner, towards the end of the date, she told me a bit about her former 

relationships with two guys she loved (one was the guy she was with
for 3 years, another was

apparently a married guy who she had an affair with on "accident").
After telling me this, I

just sorta lost something in my attraction to her. I've personally had
to face the idea of

someone cheating on me before and it killed me inside...and here is
this person who was one

of those "cheating" people and she didn't even sound that sorry. She
sounded a tad ashamed

but not enough for her to say it was wrong, she told me, a perfect
stranger! In my eyes,

that was a warning sign of her character and possible behavior...am I
wrong for assuming

this?

I know that I may be a bit more critical because she's a date, not a
friend (for example, I

didn't expect her to get all my dorky joke/pop-culture references) and
also that I need to

keep in mind that she was probably nervous too and I'm sure she was
just saying what came

first to her...but does this bother anyone else out there? Is this a
sign of a bad match

altogether?

The night ended okay and I dropped her off back at her apartment...and
I didn't want to kiss

her goodnight because 1) we weren't in a very romantic place, 2) I
really didn't know her

very well and 3) I've always done that with other dates in the
past...I've never waited for

date two (maybe it'd be sweeter?). So, she said she wanted a hug and
it was...alright...but

I didn't feel anything then also. She said for me to call her when I
got home and I jokingly

asked, "Is it because you want to hear from me or do you say that to
everyone?" and she

laughingly said, "Oh, I always say that to people." Then, I give a
goofy puppy dog look and

say, "Oh, I thought you wanted to really talk to to me but I guess I'm
just a normal

person." She jokingly says no and that she wants me to call her (but
not because of that)

and then she thanks me again for the date.

I leave, get home, wait about ten minutes, and then decide to call
her. She thanks me again

for the date and said she had fun but sounds like she's busy. She says
she's working on

school work and I just get the impression that there's not much to
say. So I say, "Okay,

well I'll talk to you later." and she says "Okay, goodnight." and
that's it. Feeling stupid

and like I maybe missed my chance to ask her out again (no harm in
keeping options open,

right? - at that point, I still wasn't sure about what was going on),
I call her up like a

minute later and say, "Listen, truth is, I wanted to ask you out on a
second date, but I'm

scared sh*tless...I don't know what to make of all of this...and
you're not like any other

girl I've been out with so far...and it's not that I'm not confident,
I'm just nervous about

meeting someone different...and it's really throwing me for a loop on
what I'm supposed to

do. But honestly, I want to go out with you again." She said "Yeah,
that'd be nice" and then

said I could call her up to set up another date.

As soon as I get off the phone though, I just feel like a retard. In
one way I was really

scared by the idea that I couldn't make sense of a seemingly good date
and telling her

seemed like the honest and respectful thing to do, rather than giving
her the idea that I

didn't like her...on the other hand I was furious at myself for sounding the way I 

did....not necessarily needy or desperate...but not confident.


What the whole point is in this long @$$ rant is, Is this really worth
trying for at all? Is

it really too early to tell? Do I have major clues in front of me of
what's to come? Am I

just analyzing stuff to death instead of enjoying the moment? Am I
kidding myself thinking

this girl's a keeper when I could be out trying to date another girl
(FYI, I only date one

girl at a time even if we aren't a couple yet) Is the lack of real
emotion attributed to us

just not kissing yet and still being in a "first date" zone? Am I just
trying too hard with

this relationship to make something out of nothing? Or am I just being
too hard on myself

and my date?

In the past, I have analyzed my girlfriend or date a lot and while I
don't try to, it's just

hard. I'm almost always right and luckily I get out before things get
horrible...but I

really want this girl to be different. She seemes different and for
the first time in a long

time, I'm not 100% convinced I should or shouldn't pursue a second
date. Maybe not knowing

what to do means you're on the right track? I dunno!

I just anyone out there to give me some advice on maybe what to do,
what to avoid in future

relationships, maybe an opinion on whether or not the "questions
before the date" thing is a

good idea, etc.

Above all else, tell me what you'd do if you were in my shoes based on
what I've told you.


Thanks!