The bartender is gonna tell Ashley what he saw.
Concur.
And what was said. And, depending on how good of a read the bartender has on general dynamics (most long-term/good bartenders pick up a ridiculous amount of basic psychological theory), the significant difference in interaction. Ooopsy.
Also concur. But if I know anything about 19-year-old women (and I probably don’t), this will only make her want you more.
Subscribing, so that I can find out how the soap opera works out.
[Voiceover] Will the bartender tell Ashley? Will Laura catch our hero with Ashley? And what about Laura’s kids? [/voiceover]
Allow me to offer my sincere advice … 
With the possible modification of “threesome!”
Nineteen-year-old girls who give you a hard-on always seem much more mature than they actually are. You want her to be mature so you feel justified in fucking someone who is half your age.
Luckily you fixed the problem when invited Laura to the pub.
Cuckoorex, I’m really disappointed. I’m not sure I’m rooting for you anymore. You’re nearly 40 and you are setting up a rendezvous with Laura while Ashley is sitting right in front of you? You shouldn’t even be checking your texts while you’re talking to her, not to mention replying to them. And you’re meeting Laura at Ashley’s workplace?
You shouldn’t have replied to Laura’s text until you got home, and then arranged a meeting at a neutral location.
This is all kinds of bad. You’re being way too reckless. You need to get a grip. Stop thinking about and discussing these things so much and just start behaving like a standup guy.
Well, after reading your update I have to completely agree 100% with your topic title: yes, you’re pretty much an idiot. Dog, bone, reflection in water, etc…
I think you’re doing great and both are potentially into you, but just try to relax more, don’t micro-analyze everything. 
Bolding mine. I agree that you shouldn’t have even been checking your texts with Ashley right there; that’s incredibly rude. I know this wasn’t a formal date, but still…
And having Laura meet you at Ashley’s workplace??? Dude, that’s just plain stupid. What if Ashley had come back in? You were this close to having an episode of Three’s Company break out.
Ashley sounds like a cool chick; stick with her and see where it goes. Laura is probably best to be avoided. Unless she’s really hot, but then just keep it casual - don’t let her move as much as a toothbrush into your place, or before you know it you’ll be taking care of her two brats.
Well, she may not be looking for a sugar daddy, but I know from experience that dating someone with kids and no job can lead to a bit more drama than you may be prepared for. For instance, what do you do when she tells you that’s she and her kids are going to be kicked out of her apartment because she can’t pay rent this month? You’ll either feel like an uncaring jerk for not offering to “loan” her the money, or you’ll feel like you’re being used for offering to “loan” her the money.
While keeping it casual is good advice, I don’t think we have enough evidence to conclude that she’s looking for a Replacement Daddy.
I once had a really fun friends-with-benefits situation with a divorced mother of two which lasted a couple of years. I rarely even saw the kids, and she never had any designs on a more serious relationship. It was pretty great.
And I’ll take this opportunity to repeat myself and advise Cuckoorex to *Stop. Overthinking. This. *If you haven’t already blown it with Ashley by bringing Laura to her bar, you’ve got a chance to have a bit of fun with a cool young chick, and screw a horny divorcee once in a while. As long as you haven’t promised exclusivity to either, you’re golden. Calm down and enjoy.
I’m gonna throw out some advice of a different stripe…
Do not become emotionaly invested in the “relationship” too quickly.
I’ve seen older guys fall head over heels for young girls who were just looking for a fling and some nice frind-with-benefits hook ups.
You two may end up together, but then again she might just want to bone you or just have someone cool to hang out with.
I don’t know what it is but when I’ve seen older guys get involved with younger girls they often mistake what’s going on for more than it really is.
Having said that - I don’t know you or her so none of what I said may apply in the least - only you know for sure.
I thought I had some good advice but nothing I can say will add to what others have already posted.
I guess that’s the problem with a board filled with intelligent people.
heh
I would only add that you are pretty dang brave posting this kind of detailed stuff on a public forum. I am not certain I could do the same.
My advice would be ‘go for it’ but be protected.
Haha! Wheelz, you are so committed to helping Cuckoorex not fuck this up. That is awesome.
Heh! I guess Cuck reminds me a little of myself. I’ve been happily married for years, though I do recall my single days with mostly fondness, but also a slight tinge of regret at not taking advantage of my singlehood more than I did. And yeah, I tended to overthink things sometimes. 
Please don’t have sex with both the 19 year old and the 31 year old during the same time period- if they should find out, it could do some real damage.
“Dating” multiple people is something that people from my parent’s generation did. Today, anything short of a clear one-off hookup or a mutually agreed emotionless f-ck buddy situation comes with the expectation of exclusivity. After a date or two, she is going to assume monogamy unless you come to an explicit agreement otherwise.
As for the divorcée, few things make a woman feel more worthless than discovering that the dude they are seeing is banging teenager. She’s probably already feeling pretty past-her-shelf-life with the kids and divorce. Figuring out that the guy she’s interested in would rather spend his time with someone barely out of high school could be a serious ego blow.
Sure, maybe these aren’t your responsibility. But you seem like a pretty stand-up guy.
Really? I’m 24 and. . . I don’t think this. Neither would any of my friends. Unless we agree to be exclusive, we ain’t exclusive.
That said, what with the AIDS and the herp, I do expect someone to be forthcoming with who they are banging. If you want to fuck me and someone else (and maybe someone else), that’s fine- just let me decide if the herpes risk is worth banging you.
So, if you want to fuck both of them, be sure they both understand that you are NOT exclusive and are otherwise sexually active.
It’s also possible she teaches in a private school where a BA is not required. Some religious schools require little more than a high school dipoloma to hire a teacher.