My "three strikes" against this girl I really like

It takes a special kind of person to take on a single mother…just because if you get serious, you’re not just taking HER on, you’re also taking on her child. How do you feel about children?

The ex-con thing…it all depends on what it was for. Obviously she didn’t do “hard time” or she wouldn’t be out and about…but there’s nothing you can be convicted for that wouldn’t raise a flag, really. Drugs? Theft? Accessory to…? It isn’t fair, though, to “convict her” of any of these if your source is only semi-reliable.

The smoking thing…either you put up with it or you don’t. Do not ever get with a smoker assuming they’ll quit. That’s up to them, and it isn’t fair to either of you to assume otherwise.

As for her being a co-worker…while I’m not discounting it, I don’t see it being a big huge deal unless your company has a policy about it.

None of these things are insurmountable if you like her. And the only way to find out how much you like her is to pursue her. If you’re just thinking of her as a casual fling, then by all means cease and desist. But if you’re attracted to her–physically and mentally–what’s the harm in hanging out with her and seeing where it goes?

I don’t think that is really fair. When a person first attracts one’s eye, you often know very little about them other than that they are “hot” and you seem to “get along”.

The issue is I think whether it is worthwhile to put in the effort to get to know more.

How do you know what is worth her time? Women like sex too, you know.

I’d try to find out whether the prison stay turned her bi before making the final decision.

Erm… I don’t know about you, but while I wouldn’t date an asshole who was hot, I’m also not interested in dating nice people who don’t turn me on.

The pantal reaction is *always * a determining factor.

Co worker? Depends on how closely you work together. My company is big enough that there are many coworkers I’ll never encounter as part of my job.

Ex con? Yikes. That’s a big red flag for me. If it were something like a teenage possession charge, maybe it would be okay. Maybe. But mostly it would be a dealbreaker for me.

3 year old kid? Doesn’t bother me, but it’s fine if it’s a dealbreaker for you. Dating someone with kids means you will always come 2nd to the kid. If you get serious, there’s another person (the kid) involved in the relationship. You need to be able to handle that.

Smoker? As long as they don’t smoke around me, I’m okay with it. But, as others have mentioned, don’t plan on her quitting.

Only if shes a drama case or you are. I have had a couple relationships with co-workers my twin sons mother was one of them.

The charge is the big issue here but either way, jail time of any real duration can be kinda a life changing ordeal. I have dated several women who have done a few days or weeks here and there for DUI or drug posession. If we are talking years, that would probably be a deal breaker for me. You don’t go to jail for 1 year plus from little victimless first offense crimes very often.

The presence of children is IMHO expected in almost any woman over 25 or so, or who was previously married. People have kids. Her relationship with dad and or her family will be more indicitive of problems. Heck my grandparents see my kids as much as I do.

I have dated a couple smokers, don’t expect to change them.

The biggest piece of advice I would say here is, ask her out. You are getting yourself all worked up about what you like/dislike about her when she might not like you enough for much more than to mooch free starbucks off you.

Its not like you are putting a down payment on a house together, and picking out china patterns.

The thing about dating a coworker is that for the length of the relationship it ususually isn’t an issue - as long as there aren’t any policies about it, its not a supervisor/subordinate thing, it doesn’t set off people’s morality buzzers (if one party is married for instance) and its conducted with discretion. And ending usually isn’t a problem, if that too is done with discretion. However, there are people incapable of being dumped without creating major drama around the occation. For instance, if you happen to be a city councilman (true story) your former campaign manager/former mistress choosing a city council meeting to tell you exactly what she thinks is wrong with you can create issues in your career. Even at lowly peon levels, its often easier to let two people go than to try and figure out who exactly is at fault for disrupting the business with relationship drama. I’ve told the story before about the secretary I worked with who got drunk on the day she gave notice during her farewell lunch, and walked into her Senior Director of Fortune 500/newly married (within months after dumping the secretary) former boyfriend for a rather loud heart to heart.

Don’t you be rolling your eyes at us when we’re just answering the question you asked. Getting defensive because people are reading things into your question is pretty touchy - you ask a personal question here, you get personal answers.

{Holy crap, I really have become my mother!}

Well someone has to date the smoking ex-cons . . .

Sorry, I mean I don’t really know that much about her, it’s only been about four days. And we don’t get to talk that much.

The rolleyes was more because I felt like you were accusing me of doing something wrong, or just looking for a one-night stand. Hell, I do allow Professor Wang to guide me sometimes, but I don’t wholly go by that, and I would like to avoid big, obvious pitfalls where I can.

If I don’t see them, I ask someone else who might. Do I think she’s hot? Yes. Do we seem to get along when we talk? Yes. But I don’t know that much about her. We’ll see.

Or, maybe the OP backed off on his “really like her” because he doesn’t “really know” her like he states now in post #30.

I’ve noticed with a lot of these types of threads, people (men and women) talk about wanting to date someone and attach these feelings to them as if they are well acquainted with the person. What it really boils down to, in many of the situations, is that they are just really attracted to them. That’s a big difference in adult-land.

Now, I’m not saying it’s wrong to be attracted to someone. Like someone mentioned above, not too many of us are going to go out with someone we find unattractive. It’s just hard to give advice or an opinion on a situation when you’re not getting a clear picture of what the situation really is.

Reading the OP, I personally got the feeling this is a girl he’s been working with and with whom he shares a good rapport. The new information is that he really doesn’t know much about her as he has known her four days and they don’t talk much. Those are two very different situations.

There was a recent thread where a man wanted to ask out a girl he met in training class. In that thread there was much agonizing and kvetching about should I?/shouldn’t I?/what if/how will/etc. I don’t mean to single out that OP or the OP in this thread. It just seems like people attach more to the situation than what is there. If you build it up in your mind, it’ll be easy to be disappointed. What it comes down to is that you’re asking out an almost stranger. Not much to lose in comparison to asking out someone you’ve known for awhile and may lose the relationship you currently have by moving it to a dating situation.

If they say no, then you’re not going to have a dating relationship with this person you barely know. Putting it into perspective, you’ve lost out on very little. Sexual attraction can happen instantly, and there’s nothing wrong with it and there’s nothing wrong with wanting to find out more about them. But, let’s not make it more than it is. You’re only going to cause yourself anxiety and trepidation.

Sounds like she’s a good drinking buddie in a group setting, not a potential GF.

Just have fun with her in that capacity.

Yeah, that’s good advice. I’ll try and get to know her (and about her) and form a more complete picture before I suggest anything possibly romantic. Thank you.

I’m moderately amused that a number of people seem more shocked and disgusted by the smoking than by the jailbird past.

Jail is not a yellow flag. It is a red flag. I’ve done some colossally stupid things in my time, but never come particularly close to being sentenced to time in jail (I may have come close to spending the night in jail for some minor-in-possession or the like, but generally the light misdemeanors don’t lead to an actual sentence of time, more like fines, community service, etc.). In short, she did something really stupid at some point. So, she’s an outlier.

Outliers can be fun. But generally, outlier behaviors, especially when clustered, don’t spell dating gold.

You do realize that there’s a middle ground between friend and girlfriend.

True. That’s land I’ve never explored, however. Didn’t say I didn’t want to, just know nothing of it.

Fuck buddy?

That is what I would try for in his situation…