I think I identified the source of the problem for this.

I've seen at least two threads on here describing the problem. When you "age up" a Sim on their birthday, Freetime is supposed to allow you to age-up up to three townie friends, as well. However, some people (including me) have had problems where the dialog box doesn't open to ask you to name friends to grow up.

After a lot of diddling, I traced the problem down to "agecons.package", a hack that is supposed to let you change the number of years it takes for a Sim to go to the next age. For instance, in my game, I used to have it set so that teenagers only took seven days to become adults.

There are different variations of aging hacks out there, so you'll have to identify them yourself. I made my Agecons.package hack by hand using SimPE with the directions on Inge's site for extracting it and tweaking it. I never distributed it, but I know for a fact there are many versions out there in use.

To summarize: Modifications of the aging constants (like agecons.package) made prior to FreeTime are likely to screw up your game (only slightly) so that when your Sims grow-up, they don't get the option to grow up their townie friends. Mystery solved.

.....

Other gratuitous observations:

Now that I have got it to work, I was disappointed that when you grow your friends up simultaneously, your Sim falls out of love with his/her townie sweethear who also grew upt. I had kind of hoped that they would keep that red heart thing going. There are so many hacks and cheats for growing up townies already available that it seemed like the only way for EA to make it interesting. So, it's not that big a deal.

Another observation: When you grow up townie friends to adulthood, they become unemployed. That sucks.

Well that stinks - I've just tweaked my age cons and put it back into my downloads folder (and by only just, I mean just a minute ago ) I've been really excited about it too - the last time I had a elder, she was still alive by the time her daughter became an elder >

Does this even include the FreeTime version Inge has up for it?

Oh my goodness... how come I've never heard of this hack?! Can anyone link me to one please?

I hope it's okay to link - http://www.simlogical.com/sl/Sims2Pages/Sims2_Aging.htm
Go down to Age Group Tweaks, but you have to adjust them yourself :P

Thanks! I really needed something like this ;D

right now there is not a free time update for the insim.

Come to think of it... i have not once been given this option since I got Freetime. It could have something to do with the fact that I don't play very many neighborhoods with townies.. or a conflict. I should check. Thanks for posting this.

I get the option, but I don't have that hack. Thing I hate about it, is that the selection of people to age up seems completely random.

Huh?

I never had any problems with choosing townies to age up with a sim as well, but then I pulled out the age cons hack just after installing FreeTime. It seems logical that the hack will effect this feature though so I'm not going to start up my game to see if it's related - I'm sure I can handle having elder sims live longer than my adult sims :o

When do you get the option? Just when teens or older grow up or when children grow up also?

I had a child grow up the other day and the dialog came up asking if her one townie child friend wanted to grow up with her. Pretty neat!

Children, Teens and Adults can all do it. So let's say I got Savanna Ritchie, a playable child sim to age up with Brittany Parker, townie sim. It's kinda cool for brritany and Savanna to age right up to Elders, unforently Elders can't age thier elder townie friends and have them be killed of oldness too.

Not true. I grew up a teen Townie to adult, got my Legacy heir to fall in love with him and marry him in, and he came with a ton of skill points and a position as Captain Hero.

Yeah, I noticed this, too.

When you age up a townie, and if you later ask that townie what his job is, he'll say unemployed. However, if you move that townie in or marry that townie, he/she will suddenly acquire a very good job.

You could always solve that problem by manually killing the elder whenever your sim dies. That way you don't overpopulate with elders.

I didn't get the option either, and it turned out to be squinge's "TeenToYoungAdultNoCollege" mod, which sucks because now I can't have my YA's attend college from home. Anyway, just wanted to let others who might have this problem know.

I have four or five NPCs have grown up with my sim kids and now they are in collage all together. I let them stay with my own two sims in a dorm. Two of them even fell in love. But I don't know what to do with them after the graduation.

Actually I want them to be NPCs again because I don't want to play with them after all.

I just got FreeTime, and no one has had a birthday yet.
If on the child to teen birthday you pick a friend to grow up too, will that same friend automatically grow up with your sim for all the future birthdays too?

I don't have this hack or anything similar and it still doesn't work anymore like it used to work a while ago. That's strange.

There's no automatic aging; you would have to select the same friend to age in the next two transitions. Also, if you have Uni and send your teen to college, no dialogue for townie aging occurs at the teen/YA transition, so the chain is broken unless you send the townie teen to college.