What are some things a young, "model-pretty" 20-something woman might like about the idea of dating a 39 year old guy who has stuff to offer-- money not being one of them?

Forget about what you have to offer and talk about her, her family, her pets, her childhood, and especially, her father.

If forced to answer questions about yourself, start every sentence with “Who me? I’m nothing special. I’m all about you.”. Then curve the conversation towards a fictional story about a lost puppy, and how happy the handicapped child owner was when you returned it… freshly groomed.

Keep your car immaculately clean.

Arrange for friends to call you while with her… Repeated say “That’s unwise… That’s dangerous and foolish… When will he ever learn”.

Keep your car cleaner than your mouth.

Compliment her music.

Put a piece of artwork in your back seat, but only after researching the artist… someone provocative.

Have fun with her until the day she breaks your heart.

20 year old women often are attracted to men that are responsible and mature compared to the 20 year old men all around them who are drinking beer bongs and not serious about life. If the older guy makes them feel beautiful and he is genuinely a nice guy, that is very attractive.

Some women are attracted to much older men for the whole daddy comple, oedipal thing. If you believe that type of psychoanalytic stuff.

I’ve met several 18 to 21 year old girls at work recently (and at school and other workplaces in the past) who wanted to go out with me. I’m right around the age described in the OP, close to 40ish, and I just don’t see what I would have in common with girls who didn’t even experience their bar scene age yet. I’m also a very introverted guy with more introverted interests, and I’m not looking to play the role of daddy or sole financial/emotional health provider to a much younger girl who doesn’t even know what she wants out of life yet.

I’ve provided you with a post stating why as a guy in that age bracket that I’m generally not attracted to much younger woman. I’ve likely inadvertently answered your question _What are some things a young, “model-pretty” 20-something woman might like about the idea of dating a 39 year old guy who has stuff to offer—money not being one of them?_by describing my own turnoffs.

You can give them the emotional support and emotional security that they can’t get from a younger guy, regardless of financial status, so that would likely be considered to be a plus in their eyes. I have to ask you this though, for your own sake here, can she offer you the same things back? Just like women, men have different ideas about what’s important to them in a relationship so I’m sure there are many guys (maybe even yourself) that would disregard my advice as well.

I don’t know yet what she could offer back other than a friendly face and a new experience. I guess one other thing in that I didn’t really date when I was that age due to some severe depression, and the element of playing catch up with someone like her has lingered with me for a long time, although that idea has kind of lost its luster in the last year or two. Yours is a good question. I think for me the time right now is about dating casually and broadly, so she fits that criteria. She’s a nice girl and that goes a long way with me at any age.

Men mature slower than women. Most 20-year-old guys act more like 10-year-old boys. A 30-something guy is more likely to be mature (maybe) and independent (hopefully), both of which are attractive qualities.

On a side-note, I’m 23 and, while I’m married to a man my own age, I find men in their 30s and 40s to be very attractive. In fact, I can’t think of a celebrity under 30 that I find all that appealing. And I obviously won’t be dating any of them, so it’s a purely physical attraction. Many men age beautifully. So, it could be that she’s just a weirdo like me and it has nothing to do with maturity or independence.

You won’t know until you give a go..in my experience it takes a long time to get to know someone… and some people who seem the most genuine at first might not be…and vice versa…. I hope it works out for you :-)

Well, everyone has a fetish.

Assuming this has happened to you as described, part of the question you need to answer is, “What does she have to offer to you?” That is, aside from being “model pretty”, which I admit is a nice quality to have in a paramour, what else is there for you in this relationship?

Because if all she has to offer is a pretty face and, one assumes, regular sex, then maybe that’s all this is about. Maybe all she wants is an uncomplicated relationship that’s more on her terms, sex when she wants it and no future plans to worry about.

However, having been on both sides of your dilemma, I can tell you that a lot of younger beautiful women are tired – really tired – of only being complimented on their looks, as if that’s all they have. (For some of them it is, and it’s sad when they find that out.) If you’ve got one of the young women – and there are tons of these out there, too – who is beautiful and smart, talented, ambitious in ways that don’t involve being a gold digger, etc., then be certain to notice those qualities in her and help her to develop them. As others have said, she may just be looking for a more adult relationship than it has been possible for her to find among young men who “are only looking for one thing”, and only see her in that light.

And more than likely she does have some unresolved issues with her father.

Experience of the world
Kindness
Thoughtfulness
Sensitivity
Good conversation
Sense of humor

I don’t think I would ever have described myself as “model pretty” but I suppose I used to be relatively attractive..(now I’m an old married hag. Ha!)

When I was 18 to 25 I consistently dated guys at least a decade older.
As other posters have pointed out – girls tend to mature before guys do – so the 29 yr. old that I dated at when I was 19 was actually a pretty good match from an emotional maturity / mutual interests point of view.

While I didn’t marry any of the much older guys that I dated (in the end the guys seemed to “catch up” with my maturity level..so by the time I was in my late twenties I started dating guys closer to my own age)..I can tell you what my takeaways were from dating the older guys that I did…

In order of the older guys I dated, here is what I “got” from the relationship:
1. One taught me something NSFW (..which every girl should learn)
2. Another of my older beaus taught me the sad, but necessary lesson: “Never make someone a priority when all you are to them is an option.” (BTW, this is a Maya Angelou quote)
3. To take risks and never stop being playful (and this I learned from two different beaus—one taught me to drive a motorcycle, the other helped me break into an Observatory..where we found an Astronomy grad student willing to let us join him to look at far off galaxies for the night)
4. Married men who attempt to woo single young women (especially those in their employ) are true cads. Avoid at all costs!
5. One taught me about antiques, another bought me some furniture
6. Yet another beau taught me how to golf
7. One took me to a gun range and taught me how to fire a gun

So..good luck to you with this attractive young woman. No offense intended when I say it’s unlikely to last…but if you aren’t a narcissistic a-hole and you treat her well..maybe it’ll go well.