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!

---

Clarification of Question by scottcc-ga on 16 Jan 2006 21:33 PST

Let me just add something to this that I may have left out...

This girl is actually very nice and very sweet. I actually find her
different past and outlook on life refreshing because in reality, I
probably wouldn't truly like someone with the same past as me. Plus,
she's really pretty and is 27...a nice change from the teeny bopper 20
& 21 yr. olds I usually snag. She's a nice person, and I don't think
it's an act.

The 3-yr. relationship with an ex thing bothers me the most because my
first love shared that similar background and whenever I encounter a
girl will that as her baggage, things never seem to turn out well. I
don't know if it's my subconscious making that into a huge issue or
just a sign of how people who have been through that will be as a
girlfriend. I'm just always afraid I'll be a rebound and just tossed
aside if an ex or something better comes along. It's not always my #1
focus, but it's always in the back of my mind.

I also know that because in the past I was tossed aside by a few girls
after they were done with me (namely first first love), I tend to find
excuses and reasons why a relationship isn't working in order to be
the one leaving first. Yeah, it's true I'm almost always right in
someone being a good or bad choice for me...but does it have more to
do with me really seeing that or picking out pursuing someone that is
wrong to begin with?

This is sooooo confusing. I'm usually so on-the-ball with other
aspects of my life. Dating just always seems to kick my butt and ask
questions later.

"Am I just analyzing stuff to death instead of enjoying the moment?"

Yes.

Hi,

You sound like a guy that is very aware of what is going on with
yourself and your environment.  With that perspective in mind, think
of it as trials of life.  Go with it.  Easier to say then to do,
especially since I?m not you in your situation.  The only real
blockage that I can see is that you mentioned you have a problem with
her 3-year relationship.  Everyone has baggage to bring to the front
porch, it?s not just relationship based, I?m not quite sure what is
bothering about it.  Your subconscious does play a part into the whole
thing, it will carry forward and affect the outcome ? so you have to
let that go.  You?re afraid of being a rebound and tossed aside ? you
have to let that go or that is what is going to happen.  You can not
think that an ex or something better will come along because you can
not compare yourself to others, no one can be better than you, just
different.  Plus you need to have the confidence to say that you are
your own man.  Yes it?s true, women will play with you and toss you
aside like an unfinished dinner (hehehe ? only joking), even if that
has happened in the past, not quite sure of the pattern that preceded
the situations, you gotta keep on going.  To me there it sounds like
you are aware of yourself, also that is a defence mechanism to protect
you from the emotional stuff.  But you are much stronger than you were
before and you can handle it.  The main thing is that you are thinking
too far ahead, about being in a relationship, having a pet, sex,
having a kid, a mortgage, all those couple things.  It is great to
think about those things because it is heaven to be in a great
relationship.  Be cautious when pushing too hard.  I?m not quite sure
what your belief system is, but love is a very strong force.

The only non-professional advice I can give you is to not think about
it too much.  Take the chances.  Enjoy it for what it is and let it
develop.

These are only words, what they really mean is that there are people
there that love and support you no matter which path you take.

All the best.

I think you need to take her to a carnival for your second date. You
need a nice long roller coaster ride. It's virtually impossible to NOT
live "in the moment" while on rides....plus it's a LOT of fun!

My favorite ride is the superloop! 
http://www.italintl.com/images_db/Superloop-2.jpg

How many red flags do you need?

1) You disagree with her morals (she dated a married man)
2) You suspect her of lying about her involvement with her ex
3) She's on the rebound (You don't want to be her rebound relationship)
4) You think very little of her intellect and interests
5) You're not really attracted to her... no sparks
6) You have plenty of work to do with your own baggage, let alone hers.

Listen to your gut and run for the hills!

I'm with Sublime on this.

Dude, chill out. I'd never get out of the house with all that stuff in my head.

So far, thanks for the comments...mostly :)

To sublime1-ga, while a simple one word "Yes" seems like a clever and
breakthrough answer on your end, it does squat for me. Even if I am a
person who analyzes stuff to death are you saying that none of the
stuff mentioned wouldn't be on your mind AT ALL during a date? So
please, while I agree that yes, I analyze things a lot, I would
appreciate more detailed feedback either on that subject or something
else besides that. One word answers with me don't go very far with me.

To artist_perspective-ga, I'm glad you wrote back with a fairly
detailed comment. It's nice to hear that maybe I am just not living
"in the moment" and enjoying things like I should, especially on the
first date BEFORE there is even a relationship. I was really thinking
that, but if an outsider can clearly see it, obviously I need to work
on that. But what would YOU do if faced with all that knowledge about
someone? Being a possible rebound might not be a big deal to most
people, but I don't just date to date. If I start dating someone, it's
with the intention of having something more than a brief fling with
them. I'm not exactly 18 anymore, I need to start thinking more long
term in lots of things that I do. Are you saying that if you met a
girl/guy who had just come out of a long, serious relationship you
wouldn't have second thoughts about maybe what to do?

To cynthia-ga, life isn't like a TV show or movie. The problem with TV
shows and movies is that you see a relationship build over a quick
montage of scenes wehere love blooms instantly and most of it is done
through little or no talking. A carnival/rollercoaster ride is a cute
idea, but hardly a solution to the real issue: Is this someone I
should be pursuing? And since no one can really answer that for me
100%, I'm asking you, would YOU see what happens with someone like
this or just cut your losses now?

To gabrielleadams-ga, thank you. I know most of the time people tend
to answer their own questions while they talk, but it's nice to see
that someone else clearly picked up on the stuff that was bothering
me...which means you at least READ my rant! :) Now, my question to you
is this, do you think I should look at someone's past if I'm with them
right here, right now? Should a person's past really play any role in
us together now, or does the wiser man look behind before he moves
forward? I don't want to be judgmental but at the same time I don't
want to be someone's play thing. What do YOU think?

To markvmd-ga, yes, I probably do need to chill out. But keep in mind
I don't go out on dates every Saturday, my goal isn't to score with
every lady that walks by and I try to keep myself out of relationships
that may go sour quickly for obvious reasons for both people's sake.
So yes, while I will chill, I really hope I'm not the only person out
there who likes to think a bit ahead about someone I'll be potentially
spending most of my time, energy and resources on.

Thanks for all the comments so far, keep 'em coming and someone will get paid...!

Live in the moment, you will rarely regret having tried and will
usually always regret not having done something!

2 quotes - 

It's better to regret something you have done than something you haven't done 

"Regret for the things we did can be tempered by time; it is regret
for the things we did not do that is inconsolable."

Go for it, stop analyzing it to death and take a chance - worse case
scenario, it doesn't work out and you move on. You aren't that old,
there is lots of time to find that right person.  Enjoy trying!

mom2my2boys123-ga,

You ARE right. Screw it, what the heck! The WORST that could happen is
I lose a couple of weeks on this girl, maybe develop feelings for her,
maybe have a lighter wallet for awhile...really, you're right. I'm no
Mr. Perfect and I have baggage just like everyone else...and yeah, I
guess there IS a chance I could get my heart broken...but in the end,
that's a small price to pay for a chance to hit it off with someone
great, huh?

Wow. It's amazing how a sentence as simple as "Regret for the things
we did can be tempered by time; it is regret for the things we did not
do that is inconsolable" can really make my day.

For once, I'm glad I analyzed this girl to death...because maybe I'm
starting to realize that doing THAT gets me nowhere. She's different,
and I have a feeling now she's worth the risk of falling, good-or-bad.

Thank you.

When I was young and single, I put myself through a lot of boredom,
unpleasantness, and heartbreak because I had the misconception that it
was better to have a date with someone - anyone - than to stay at home
alone.

I agree with gabrielleadams. Run for the hills.

In response to pinkfreud & gabrielleadams, I'm a little....

Dammit! I'm not a LITTLE confused, I'm A LOT confused. 

Despite my momentary enthusiasm after reading about the "things you
might regret" post, I'm leaning back towards the side of reason, the
side of acknowledging that honestly, I believe I'm just trying to make
something that doesn't work work, simply so I have someone instead of
no one.

Weird thing is, I didn't use to be this way. All through college I was
happy and content with myself, sure I'd get lonely now and again...but
for about 90% of the time, I was okay with just me. Now, ever since
I've had a taste of relationships, for some reason I'm drawn to them
like I magically need them to complete me. I'd say dating (or thinking
about) now takes up probably 40-50% of my time, energy and resources.
It's actually quite frustrating not being content with how I used to
be and always feeling like something is "missing."

This girl is nice and sweet and she may have been a great catch at a
different point in my life. But I think I'm just going to step out of
the dating thing for awhile (and this time stick to my guns about it)
and get myself back to working order so that I don't feel like I need
a girlfriend in my life to be happy.

Hmmm, surprisingly helpful discussion. Mostly me just blah blah
blahing on the internet. Nice feedback though.

I still will take the "regret" quote to heart, but I think I'll bow
out in regards to this particular girl. There are plenty of fish in
the sea....and while I have no intentions of courting an actual
aquatic creature, it'd be nice to date a girl who likes Seinfeld.

:)

scottcc,

I can't teach you this, since it is something that each person needs
to learn for himself or herself, but you do not need a relationship in
order to "complete yourself." Having been married for over 25 years, I
am intensely aware of the benefits of a loving relationship. A
relationship can be a wonderful and life-changing supplement to one's
self. But the notion that it is a "completion" usually stems from
insecurity about one's worth as an individual.

You're complete already. The relationship is the icing, but you're the cake.

mom2my2boys123-ga seems to have taken you where I was pointing.

Now I'll elaborate a little. Excessive thoughts are the judgments
we impose between ourselves and 'what is'. They are the dark
glasses through which we perceive everything around us, coloring
our perceptions so that the world appears as we think it will.
This is the source of the self-fulfilling expectations which
most of us have, and to which we confine our experiences, and
condemn our souls.

This tedious practice keeps us from experiencing things 'just
as they are', and precludes the magical possibility that a
person, place or thing will, in this very instant, transform
itself into something other than what we have known and judged
it to be.

Labelling things is the essence of this judgment. When you
stop labelling a tree as 'tree', it becomes, instead of
a one-dimensional word symbol of a two-dimensional image symbol
of a member of the plant family with thousands of variations,
it becomes a wondrously unique three-or-more-dimensional
individual entity with details which you could spend the
rest of your life becoming aware of.

The same thing occurs when you stop labelling a female as
immoral, lying, rebounding, stupid, and uninteresting.

Harry Palmer said, "Love is the creation of a space in 
which something is allowed to evolve".

Now don't get me wrong. I'm not saying to ignore your
best interests. I'm saying that your intellectual approach
to analyzing her is simply not as effective as allowing
yourself to spend time with her, using your feelings
instead of your thoughts. This means eliminating thinking,
since your thoughts will cause you to have feelings which
prevent you from actually feeling what is in front of you.
Stop thinking, and there is nothing you will not be able
to know about her, to paraphrase the Book of Nothing:
http://www.deeshan.com/sosan.htm

You've fallen into the trap of most of modern society,
where you don't want to invest your time, attention and
money into going to a movie unless you're sure it's 
worth seeing, so you seek the opinions of others who
THINK like you, and JUDGE like you, and only go if they
agree it's worth it.

The fallacy of this is that you're a unique individual,
and a certain look on a certain actor's face in a certain
scene of that specific movie which your friends have
panned as worthless, may be the perfect trigger for a
tremendous personal realization on your part. But you'll
never know that if you don't see the movie, or worse, if
you do see it, but through the lenses of your friends
judgments - so you don't really see it at all.

If you want to pursue an excellent path toward eliminating
thoughts and judgments which limit your experience of life,
I heartily recommend the Avatar Course:
http://www.avatarepc.com/

There are free mini-courses available for download:
http://www.avatarepc.com/html/mini-eng.html

You can also download a free PDF copy of a book by
Harry Palmer, the author of the materials, which is
used in Part I of the course - Living Deliberately:
http://www.avatarepc.com/html/eliving.html

sublime1-ga

Hey, having a second date isn't like seriously courting her or any
kind of commitment.  If you think you can have a good time and don't
have anything better to do, plan something that you both will enjoy
doing without all the deep questions (better to let her  - and you - 
forget that).
I don't think Rollercoastering in January in Chicago is so good, but
do something and don't have it end with an obvious "you want to come
up and see my designs" situation.  That way, either of you can back
out more gracefully, or if neither wants to, then you will have gotten
answers to a lot of your questions.

When you think about, you could worry about all the baggage the way
you have with any and every girl.

Good luck  (and don't ask her if she knows about G-A!)

I think you're smart to at least be thinking about areas that could
create some incompatibility in future between you and someone you're
dating, or thinking about dating. Now some people are just socializing
and having a good time, and for them, sure, enjoy the moment and chill
out are good advice. But I suspect from your question that you are not
one of those, and face it - dating is for most people a way of looking
for a mate. It sounds to me as if you're using dating as it's
traditionally been used. That is, you're "auditioning" various
candidates to see how well (or poorly) they might function in the role
of mate for you, which is certainly an appropriate and understandable
position for a young man of your age and status. So ok then, just
acknowledge that's what you're doing and then get on with it.

On to specifics: one concern you expressed is being bothered by this
girl's intelligence -- or rather, lack there of. Believe me, that's
important! And you're wise to be aware of it.

Fact is, when you're dating, and caught up in "fun" and hormones and
all of that, it's easy to lose sight of the things that are ultimately
more important, things like being able to carry on a conversation with
someone whose intelligence level is about equal to yours. And yet
those are the things that really do matter in a long-term
relationship, or in a marriage.

I'd like to recommend to you an article (or more, your choice) written
by a marriage counselor who has spent decades - and has a phenomenal
success  rate - helping couples to repair troubled marriages. He's
written several articles on what to look for, what to consider in a
potential mate. And although if you marry without taking these matters
into consideration, that's not necessarily a predictor of doom, by
considering these things ahead of time, you do significantly stack the
odds in your favor.

According to him, the five most important areas in which you should
have compatibility or similarity are:

1) Intelligence
2) Energy Levels
3) Social Interest
4) Cultural Backgrounds
5) Values

See here for a further explanation of these, as well as links to
further reading if you so choose:
http://www.marriagebuilders.com/graphic/mbi5068b_qa.html

And good luck to you. As a post-middle-aged grandmother, married for
the second time, I can only say I wish more young people were as
forward thinking as you. Keep analyzing. It's not a fault!

Best wishes to you,
Byrd-ga

1. I think the invetagative approach is a good one as it stops you
from getting hurt so much, however, I think you got too deeply
involved in this method and you don't want her to think you are overly
protective and obsessive before you start going out together properly.

2. Casually ask her when her ex boyfriend gets out of rehb and if the
two of them have mutual friends (meaning she might have to see him
again)

3. Play it cool, make regular references to a friend of yours who is a
girl and se will try and become closer to you to combat the jealousy
factor.

4. Take her out to a nightclub or live music event. If this is not
your scene or deem this innappropriate then take her to a jazz cafe or
somewhere loud so you can have a good time without having to talk too
much

5. don't ask too many questions about her background (except for the
ones I previously mentioned) otherwise she may become suspicious of
you and ask you loads of questions or it could create the negative
effect of her becoming frustrated, then she may not want to speak to
you.

follow these tips and I'm sure it will go well, most importantly make
sure you're having a good time together, if ou'renot then break it off
and find someone you feel more comfortable with.

Hope this helps you out, Toby. Site administrator for
http://www.open-your-mind.co.uk

Scott,

When it comes to decision-making, there are two types of people,
(according to the Meyers-Briggs personality type indicator).  There
are those who follow their heart; what brings them joy and satisfies
their subjective needs and there are those who take an objective
approach to decisions, even ones that inolve feelings.  The second
type tend to be analytical, objective, and need decisions to be sort
of "rational" or based on what makes "sense".  Also, this type
generally seeks feedback from peers to provide some of the
"rationnale" to help with the ultimate decision.  You've heard from
both types here.  The Feelers will tell you to trust your gut and stop
thinking so much (for example).  The Thinkers write long responses. 
(Like this one)

Neither approach is right or wrong.  

You may be the type that honestly wants to support a rational
decision. In that case, I'll paraphrase a Seinfeld episode with "It's
not her, it's you..."  Meaning, it is not her life that caused you to
question...It is the fact that you questioned and that led you to
discovery of her life.

...which led to more questions...

The question you need to answer before committing to anyone is: what
answers am I looking for? Once you know the answers you need, but more
importantly,  the answers to what you DON'T NEED BUT CAN PUT UP WITH
(because nobody is perfect); you set yourself up to recognize her when
you see her.  I mean truly "see" her soul.

Question yourself first and allow your dates to provide the answers
through their actions.

~Joy L.

You need to come to terms with your own baggage and stop carrying it
around with you or you will continue to sabotage every relationship
you begin out of simple fear.

For example, bailing out early on relationships will virtually assure
that you will get out before getting hurt by another.  Unfortunately,
it will also assure that you never have a long term relationship. 
Don't you see that 20 questions before a first date to try to rule out
a repeat of past problems is a bit disfunctional?  You're very
defensive and you would be so much better off to make peace with all
that stuff first.  One big reason is that it is so much harder to move
farward when you keep looking backward.  I know guys in their 40s who
still sound like you and don't even have long term girlfriends. 
There's always something "wrong."  What's really going on is that they
aren't emotionally strong enough to have a meaningful relationship
with another person.  Don't be them.

Maybe she's too ditsy.  Maybe she has questionable character but you
said the married guy was an accident.  If she didn't know, it's not
her fault.  If she did know, she isn't worth anybody's time.  Clues
should definitely be paid attention to but evidence usually requires
further investigation before we make conclusions.  No woman will ever
be "perfect."  You aren't either.  Unfortunately, you are letting past
experiences cloud your view.  They have no bearing on this and they
shouldn't be in the picture at all.  Don't burden others with your
baggage.  It's time to ditch it.  Then you'll be ready to be in a
relationship.

Life is going to knock you around sometimes.  Relationships can do
that too.  Some will work.  Some won't.  Some people lack character
and behave badly.  None of that affects who and what you are, and how
you behave is not determined by others.  I am convinced that to be
successful in anything a person needs to learn how to take a punch
(figuratively speaking).  How many times you get up is always vastly
more important than how many times you get knocked down.  You learn
that you can take it and you move forward able to deal with whatever
comes.  Get comfortable in your own skin and with who you are.  Then,
if a relationship doesn't work out, you'll know that you didn't kill
it either intentionally or because you couldn't deal with it...and
you'll know it doesn't diminish you in any way.  You'll find a lot of
great women but only if you are able to see clearly.  You'll make a
meaningful connection only if you eliminate all the unnecessary
interference you create for yourself.

Good luck to you.  You sound like a good guy.

Lifes for living, try not to think to much about things. At the end of
the day if its all a big mistake and you get hurt then at least you
have learnt another valuable lesson. But you never know what will
happen until you give it a go!

Wouldn't you rather die regretting something you did. Then die
regreeting something you didn't do.

Good luck! Kt

I think tossing a coin would be more time/cost effective for you.
Either choice you make you will still be haunted by a thousand
questions regarding what could or could not mean the variables x and
y, and another thousand of "why"s following them up.

Besides, I myself do not think that watching the tiresome Jurassic
Park movies (and being even aware of them) or all the 9 seasons of
seinfeld gives you an automatic 130 IQ

However, i'll give you my insights to your original concerns:

Q:Is this really worth trying for at all? 
A:How can you tell? It was only a first date, and it led you to a
second. It wasn't a miserable showcase of mutual akwardness and shame
as I see, and also, if she was such an awful person, i don't think you
would have had called her that very same night to crawl and pry for a
second date.

Q: Is it really too early to tell? 
A: It is, go and date her another couple of times, talk to her, use
the phone, use the messenger or any other chat system, even regular
mail, smoke signs, morse code... How can you tell if you barely know
the girl?

Q: Do I have major clues in front of me of what's to come? 
A: Yeap, you *might* have major clues, the real question is: Is your
sight totally unbiased in front of such clues?

Q: Am I just analyzing stuff to death instead of enjoying the moment? 
A: Absolutely yes! you can't control a wave, but you can surf it, it's
your choice, learn to let go.

Q: Am I kidding myself thinking this girl's a keeper when I could be
out trying to date another girl?
A: How long does it takes you to tell if any girl "is a keeper"? 24
hours? And why are you so concerned about investing another day on
her? I could say that she maybe is not, but I can not be sure of that,
and neither can you. Unless you tell me that you have a fatal disease
or you are sentenced by the mob and every single second is precious to
you, precious enough not to dedicate them to this girl.

Q: Is the lack of real emotion attributed to us just not kissing yet and
still being in a "first date" zone? 
A: I think it is more related to an expectations issue, appareantly
she is not what you want custom packaged in a female human body for
you. Probably you were too self conscious about the deformity on your
eyes and were in absolute shame of yourself... Maybe the settlement
and the lights were not in the right position (Just like in
seinfeld)... Who knows? only you can know the real answer to that
question. My recommendation is still the same, give her a second
chance, and a third, maybe a fourth... In the end, if you do not feel
anything at all, why bother?

Q: 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?
A: You're making a huge opera from this hyperbolic tale, chill out,
relax, have a bourbon and sit back...

My final thoughts, if in each single scenario you still end up in the
same state, paralized by this excruciating minutia of every single
minor angle and insights, why even bother in such futile thoughts and
analysis over such unpredictable things as humans and relationships?
Don't be paralized by the fact of being born in September, Just live.