OT: My dilemma, what would you do?

jester214
North Carolina
In one hand is a smoking hot 21 year old college girl. While I often have fun with her we really don't much in common and sometimes she can be excruciatingly boring. She also wants to text non-stop. It took time and some fairly expensive dates to get her into bed. She's not great in bed, seemingly inexperienced which meshes with what she's told me about her previous sex life. She partially makes up for this with enthusiasm. I'm also faced with the fact that this isn't someone I could bring to social gathering with friends and/or family. She has begun to use words like "relationship", "exclusivity" and "December trip to Biltmore". Additionally I recognize that while this isn't 'pay for play', some of my attractiveness is based on my ability/willingness to spend money on her.

In the other hand is a early 30's professional woman. I thoroughly enjoy spending time with her time with her. She is attractive but not in a drop dead sexy kind of way, (Grown men hurt there neck to stare at college girl when she's dolled up). She was much quicker to hop in the sack and so far seems happy to spend time together and fuck with no additional labels. I would happily bring her around friends and family. Her only serious con is she's been divorced less than a year (no kids) and I think there's some baggage there.

So do I keep college girl and forgo dating other women including the acceptable age appropriate lady OR do I drop the arm candy and continue to explore other options?

Keeping both is not an option. While I don't believe in pure monogamy I'm not going to actively maintain something on the side.

37 comments

Latest

Papi_Chulo
8 years ago
We all have our different wiring - for me I enjoy substance over style so the older-one would be my personal pick - I can't be w/ a dud in bed and too many hot-chicks seem more into themselves than pleasing their partner - I need to feel comfortable and compatible w/ my womenz.
Papi_Chulo
8 years ago
BTW - IMO anything chick or sex-related is not "OT"
RandomMember
8 years ago
College girl would be just for fun. Professional woman for something serious.
JohnSmith69
8 years ago
This is going to surprise everyone. Including me. My only excuse is that I'm very high. I would chose the older one. Your description of her reminds me of my DC. And much to my dismay, I have discovered that a DC is better than a DS. That's what Rech always told me. I didn't believe him until now.
shailynn
8 years ago
I would definitely go with the 30s professional one.

I have had a similar experience and the 30 something blew away the 20 something in every category but looks.

Remember the only reason the 20 something is there is for your money, the 30 something is there for you.
knightwish
8 years ago
Another vote for the professional women. Deal with the divorce baggage, in a year's time she's divorced 2 years...
jester214
8 years ago
@shailynn, I know it's not just about the money but I know it's a factor.
PRBOY56
8 years ago
Full grown woman vs. petty little girl. Lesson learned the hard way, the full grown woman for me every time !
shadowcat
8 years ago
I'd pass on both of them in favor of going to a strip club but that's just me.
JamesSD
8 years ago
Short run keep both. You're not monogamous until you Define The Relationship. Period.

Dump college girl once she starts pushing you hard to get serious. "She's not great in bed".

I imagine the divorcee isn't looking to settle down any time soon.
Corvus
8 years ago
Keep the one who is more fun.

That being said, before you dump the hot 21 year old, have a crazy, wild romp where you just have your way with her and her body. Teach her just how crazy fun fucking (or is it ducking?) can be. Do everything you have ever wanted to do with her. I'd fuck her ass too just to expose her to a different experience. Take the chance and give her a full sexual experience and see if you can broaden her horizons. If she then steps up her game in bed, then you can make a decision based on the "new her".

Just a thought.
vincemichaels
8 years ago
Don't pass up a romp in bed with Juice.

I vote for the 30 year old, her maturity will make for a better experience, young hot babes are great but they don't have fully developed brains. Brains are a big turn on for me.
IrishLad
8 years ago
I'm not sure the question is "hot young girl" vs. "attractive older woman". FFS she's 30 :-)

The way I read this the question is "committed exclusive relationship" vs. "more casual non-committal intimate relationship".

Step 1 is deciding which of those you are looking for.
Step 2 is deciding if you want what you want with the particular women offering it.

Personally, I find the idea of exclusive long term sugar daddy relationship (you made it clear hot young thing is partly in it for the financial pampering) to be a little silly. Is the idea to fall hard and eventually get dumped or to lie?
RandomMember
8 years ago
^^^Yeah, I don't really see any dilemma, but maybe the whole point of this thread is a humble brag. If you're looking for an intellectual equal you go with the older professional. If you're interested in fun, the younger girl is the choice. If you can afford both, then you can have the best of both worlds.
Subraman
8 years ago
Agree with IrishLad also. Where's your head at? The way you wrote things up, I think it's pretty clear you favor the 30-year-old and what she brings to the table.
gammanu95
8 years ago
I agree with Papi. This is not off-topic at all. It sounds to me like you want to be with the professional gal more. You can always use a variation on the coin toss. Assign the girl to heads and the lady to tails. Toss the coin. If you regret the result, then you have your answer. Works for me every time.
Subraman
8 years ago
You asked what WE would do in your situation. My answer might have been different a year ago or a year from now... but I'd go with whoever is more fun, although I can't tell from thte short description which of the two girls I'd like more. Since both girls are a bit flawed, I'd be actively pursuing things on the side -- not doing so is crazy, IMO. If I could get the 20-year-old to start thinking in terms of NSA arrangement instead of exclusive relationship, I'd definitely go that route; otherwise, probably the 30-year-old
flagooner
8 years ago
Hands down the 30 yrs old.

It sounds like the only reason you would spend any time with the college girl would be to impress other people that you don't know.

GoVikings
8 years ago
Shadowcat lolol
rickdugan
8 years ago
Jester, the answer depends entirely upon what you are seeking.

When I was in my early to mid 30s, I dated girls closer to my own age. Not because I couldn't score younger girls, but because I was looking for something long term, including someone ready to be a mother. Girls in their early 20s can be a lot of fun, but they tend to be immature and change a lot through their 20s. A 30 year old woman is generally a very different person than she was at 22. I didn't want to get serious with a young girl and even have kids with her when the odds that she would want something completely different 5 to 10 years later were just too high.

So that was a long winded way of saying that if you are looking for something serious and long-term, then the 30 something girl might be a better choice. However, if you are just playing around and have no interest in being encumbered, then you would be doing the 30 something girl a favor by cutting her loose and you could enjoy the 21 year old girl while the ride lasts.

Good luck!
jester214
8 years ago
Obviously I know that I can't realistically be in a relationship with college girl, but my little head really really wants to! Plus I have to face the fact that I'm not going to have a lot more chances to date gorgeous women almost 15 years my younger, nor is it practical. This is disappointing.

I was curious to hear all your answers, little surprised there seems to be such a consensus.

NinaBambina
8 years ago
If you simply kill yourself you won't even have to choose!
Jascoi
8 years ago
i don't pick women close to my age. shit. they're old. really old. as far as your delima... i suggest enjoy both. each has her points. and the young 21 girl is going to mature. hopefully into the dream girl.
jester214
8 years ago
Why are you so obsessed with me nina?
NinaBambina
8 years ago
Oh I'm just giving you a taste of your own medicine, since you tend to follow my posts and make smart ass (but not smart) remarks.
jester214
8 years ago
I'm pretty sure I haven't responded to anything you've posted in months. Clearly you're obsessed with me.

Maybe one day I'll be able to come up with some genius one liners like telling people to go kill themselves... That's both smart and hilarious.
Papi_Chulo
8 years ago
"... little surprised there seems to be such a consensus ..."

On the board it's easy to think w/ the big-head - if we were in your shoes we'd be thinking w/ the little-head and be as confused.
JamesSD
8 years ago
The consensus comes from the fact she's not great at sex. If she was better she'd likely get the win.
ThereAndBackAgain
8 years ago
jester you are in a situation where you should not commit to either. The teenager may just be using you as sugar daddy unbeknownst to you. You have nothing in common just curiosity of the differences b/w you.

The divorced and back to business professional seems to be a careerist who is trying to just cap her failure at marriage. I am not saying divorce is her fault but people are generally the same with a narrow spectrum of differences. Relationships are made out of compromises.

If you wan't a fuck buddy go with the more fulfilling experience.
GoVikings
8 years ago
Teenager?
ppwh
8 years ago
jester214, I would suggest that you man up a little bit and give the "boring" one some guidance on how you would like a partner to be. If she is angling for a long-term relationship, you have a position of power and can make gentle suggestions on how she could improve and gain increasing levels of your approval. I'm guessing that your reading into this as a primarily money-focused thing on her side is badly missing the point.
NinaBambina
8 years ago
Jester214 - Thank you.
jester214
8 years ago
@ppwh, I don't think it's primarily money-focused, but to ignore the reality that some of my appeal is my ability to spend money on her would be naive. My finding her boring is directly related to our age difference and her maturity. I'm not sure how that can be addressed with "gentle suggestions".

@Nina, I think/hope that's a sarcastic "thank you" but given some of your comments I'm really not sure. So to be safe, I'm mocking you.
larryfisherman
8 years ago
If a 21 year old is interested in a guy in his mid 30's, 98% of the time it's strictly about the money.
Ugluck75
8 years ago
Since I don't know either of them it is hard to say but I would choose the 21 year old since you said she is hotter and she certainly seems to like you a lot.
ppwh
8 years ago
@jester214, We may just like different kinds of women. I prefer one who likes me better and would be eager to please, even if it means spending lots of time becoming closer to her and molding ourselves to one another.

If you prefer being the rebound guy for a finished product as a diversion who wouldn't draw jealous chatter, you have your answer of who to pick. ;)
ThereAndBackAgain
8 years ago
@GoVikings ..I acknowledge my mistake...lol did I really say teenager ... I was thinking of jester with Lolita :)
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