Yeah, I'm pretty much an idiot, yes?

Very quick background info: I’m 37, white, overweight, and increasingly and disturbingly (to me) balding. Single, no kids…I consider myself an excellent uncle and I take pride in the fearlessness I display in meeting people and striking up conversations.

Recently a new grill/pub opened up downtown, about a mile away from my place. Being close and a bit novel for the newness and all, I’ve become a regular there after work. As an artist, most of my work involves drawing pretty pictures for various people and companies about town. Over the past few months, I’ve found a surprisingly lucrative market for drawing portraits at 20 to 40 bucks per, and that generally has been used as “beer money.” Not too bad. Definitely worse ways to spend free time.

Here’s where the craziness steps in and sets up shop; there’s a waitress there, for the sake of the thread we’ll call her Ashley, and from day one she’s always come over to talk to me. She’s a teacher (elementary school) and working as a waitress in the “offseason” or whatever you might term it. We have similar tastes in music, movies, TV, books, all that…and conversation is effortless. Everytime I see her, she smiles and takes time to talk to me; I’ve never been in her section, she’s never had even a dime from me, she seems to genuinely enjoy talking to me.

So far, so good, right? Myself, I never even thought about age up to this point. As far as I’m concerned, she seemed like a fairly mature, pretty young woman with some ambition and plans for the future. She asked me if I wanted to go see a movie sometime. Of course! Right?

Last night I found out she’s 19.

Now, 19 is well past age of consent or whatever, I’m not concerned about that, and obviously she’s got her head on straight, probably moreso than other women I’ve dated, but I keep thinking of the maxim about how it’s okay to date someone half your age plus 7 years, which in my case would be around 25 years old if you round down. Of course I don’t consider that a hard and fast rule, but I do feel conflicted because of the age difference. So far there hasn’t been any kind of disconnect in conversation and she hasn’t ever tried to get me to buy her something or provide anything; I’m pretty sure she isn’t looking for a sugar daddy or whatever.

As of now, we’re best described as “good friends,” and maybe that’s all that we’ll ever be, and if so, I’m fine with that. But she does little things that hint at something more; she leans against me, she touches my knee, she basically comes really close to acting like girlfriend material. She tells me her schedule and although she hasn’t said it, I get the impression she hopes I’ll be there when she’s off work.

Did I mention that she’s pretty? And young?

I was thinking that eventually it would become clear that it’s either just my imagination or some kind of puppy love, but last night…well, nothing sexual was going on, but conversation definitely got into intimate territory. She displayed a maturity that I found impressive and a keen awareness of current events and relevant issues. Even though she’s young, I can’t think of her as a child; I’ve dated women ten or more years older than her who were immature in comparison.

I’m really torn; She’s mentioned going to see a movie sometime, as I said; of course I want to. She’s pretty much asking me out on a date, isn’t she? Again, she isn’t looking for someone to buy her things; she’s kind of proud and always insists on buying her own way, be it meals or movies or whatever. And yes, she drinks even though she’s not 21 (I was drinking when I was 15, so I can’t judge).

Should I take her up on the movie watching offer? Innocent enough, I know, but is there realistically a chance for this turning into a May-December romance?

“The world is a comedy to those that think, a tragedy to those who feel.” Horace Walpole.

In all sincerity you sound like a non-asshole so just take it as it comes. Stop worrying and enjoy the ride.

I’m overthinking, right?

There’s 3 guys I can think of in my family - my Dad, my brother and a brother-in-law - who are all about 15 years older than their SO.

So yeah, don’t sweat the small stuff, just enjoy your friendship. Or whatever else comes down the pike.

Did she tell you she was 19, or someone else did?

A nineteen year old elementary school teacher? Something sounds not correct here. When did she go to college, and teacher’s college? I don’t know any teachers, who worked as servers, between school sessions, and I’ve been in service my whole life, worked in a zillion different places and live in a town with a university and teachers college.

Something seems not quite right to me.

Here’s just a dumb and maybe irrelevant question. How can she be an elementary school teacher at the age of 19?

I’ll simply offer my standard advise in such situations: Fuck her! Fuck her brains out!

I am a 52 year old guy. Ten years ago, as a recently separated dude, I was “picked up” by a cute female in a bar. We really hit it off and soon we were spending all our free time together. After about 6 weeks, a friend approached me and asked if I could hook him up with my girlfriend’s mother. I was taken aback.

Turns out we were the topic of conversation about town. She was 21. I was twice her age. And I was clueless. Suddenly, her hesitation over letting me see her DL picture made sense. She was a very sweet person, but I could not continue seeing her/sleeping with her (she had effectively moved in).

Anyway, do whatever you are most comfortable with. And keep it safe.

Yeah, I questioned that, too. Turns out she was a prodigy, graduated from high school at 16 or so, got her teaching degree the year after. Doogie Howser style and all that. She’s a smart cookie. This is essentially going to be her first year teaching, but it’s what she’s always wanted to do. I get the impression that she’s going to be a lifer as a teacher.

She sounds like a real find. I suggest move slowly: let her know you’re interested, ask her to a movie, etc. But the key is to make the move.

Hey, you’re an artist, a bohemian, fer chrissakes. You scoff at society’s rules, and play only by your own. Hell, I bet you wear a beret, don’t you?

Reminds me of that dad in Grumpy Old Men. Mount her!

Personally I’m still skeptical about the teaching aspect; she’s said that she’s a teacher but not full-time, and I don’t know the rules regarding substitute teachers so maybe she’s a sub but not full-time yet. I’m not going to do a background check on her just yet but she has named the school where she teaches, so maybe I’ll check that out.

No beret, but you’re right; I’m a maverick, and one thing I don’t play by, are rules.


If she’s really as smart as you say, then it makes sense she’s into older guys. Also it hopefully means you can count on her to be a relatively mature SO. So go for it.

Just watch your back in case she does something immature and 19ish. Emotions turn on a dime at that age.

So for you, was it the age difference, meaning the number as opposed to not being able to relate to her? I mean, you spent some time together, you must have had some conversations and good times, so did it ever come up that you had a divide, or was that just something that happened after the age difference was brought up?

I think you should be the cultural attache for the SDMB. :smiley:

You only live once and she’s obviously interested in you. Just ask her out and see what happens.

Good luck!

He does now.

I bet if I broke into your house you wouldn’t shoot me, would you?

[obscure inside joke]