David Letterman and family vacation in St. Barths

03/01/2008 at 06:17 PM ET

Talk show host David Letterman, 60, enjoys a family break with his girlfriend Regina Lasko (not pictured), the nanny, and their son Harry Joseph, 4, in St Barths on Friday, February 29th.


Photo by Bauer Griffin.

FILED UNDER: Kids , News

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Showing 22 comments

Nadad on

That’s his gf? Lolz I thought that was his daughter!

Heather on

I think that woman is a nanny and not Regina.

Dawn on

I am pretty sure that is not Regina. That may be Harry’s nanny,or a friend or a relative of the couple. Regina is in her forties. That girl has to be in her twenties. I also goggled and found this pic of Harry, Regina, and David.


Donna on

I think that may be a nanny. I think Dave’s girlfriend is older.

ellie on

That’s not his girlfriend. That’s not Regina. It must be a nanny.

emmalee on

I think that might be a nanny or sitter, not Regina. Here’s a picture of Dave & Regina:

BostonMom on

Um, I don’t think that is Regina — Regina is much older than that woman. Maybe it’s a nanny?

grace on

that is not his girlfriend! probably a nanny. i have seen his girlfriend and she is much older than that and looks way different! definitely the nanny

Rosy J on

Oh great! I finally get to see Harry’ mum. David Letterman is so in love with Harry. So happy to see them all together . Thanks CBB.

K. on

I don’t think that’s his girlfriend. She is much older than the woman in the photo.

Allison on

I’m confused, is that Regina Lasko in the pic or a nanny/friend???

Sarah, CBB Editor on

Sarah’s note: Yes, that is the nanny. Regina is in her 40s. Sorry about that, I was away from the computer for about 2 hours and was not able to correct Angela’s post right away. Thank you!

brooke on

I’d be a little bit nervous bringing a nanny that attractive on my vacation!

Pam on

I think that’s silly. It makes your relationship sound insecure if you can’t trust that your partner wouldn’t do anything. I was a nanny for many years in my 20s, I was quite good looking (although now at 38 I’m a bit past my prime!) and I never had a problem. In fact, in two out of the three families, the husbands were completely devoted to their wives and I was jealous and hoped find a husband like them someday! (I did!) Also, any responsible, respectable nanny would quit as soon as a husband made advances, and tell the wife why.

That being said, Harry is adorable. I watch the Late Show probably 3 nights a week, and I love Dave’s stories about him.

Beverley on

Hey Pam, you stated “in two out of the three families, the husbands were completely devoted to their wives.” What about the other one?

Personally, I wouldn’t have a nanny, but if I did, I would want to have a nanny about the age of Mrs. Doubtfire, because I think she (or he if you like) would have more experience than someone in their 20s.

Harry is getting big and he is very cute.

Pam on

Oh, sorry, forgot about him!! He never hit on me or anything. That was just a bad situation. He was almost 20 years older than the wife, worked all the time, the mom stayed at home, but had no interest in her kids at all. I basically raised them for 3 years. I’m sure there was some depression or other issues there. Really unhappy home.

The other families, one had two full-time working parents and preferred the girls to have one person caring for their kids at home instead of a daycare environment, and the other family had 5 kids, so even though the mom was a SAHM she really needed the extra pair of hands. All parents VERY involved with these two families.

Also, I had my LPN certificate and a Human Development/ECE degree at that age (25), and at times I knew more than the parents! (Kind of scary, actually!!)


I too am in my 20’s and I am a nanny and have been for a few years. My only work experience is in childcare and having someone (Mrs. Doubtfire) in their 60’s would be so cruel to do to your children. Someone in their 60’s lack the physical that someone in their 20’s have. I also think its silly to bring your nanny along on vacations. I can understand to an extent if it is business related but… can you not handle your children even when your family is relaxing? I don’t understand why people (especially mothers who stay at home) who still need the services of a nanny. Why did you have a child or children if you cant even handle them? LAZY PARENTS!!!!!

A. on

Not to get too off subject, but I’m a nanny in my 20’s (I’m no supermodel, but I give myself some credit) and have never found any issues with fathers and devotion, and hopefully that will continue to be the case. They have been all family oriented, with their child and their wife at the center of it all. It’s been fantastic!

For my age, I have a fair amount of experience, with day cares/preschools, and other nanny positions totaling 4 years in ‘professional settings’ (in addition to having a degree from the University of Washington).

I think it’s all a personal preference in terms of who you hire and what age, as one family told me that they wanted a younger nanny instead of a ‘granny’ nanny because she’d have far more energy and can relate to the child in today’s world. The granny nanny they interviewed didn’t know baby sign language, wasn’t CPR certified, couldn’t work all of their technologically advanced devices around the home, didn’t have the energy to go on daily walks to the store or around the lake, and could hardly move to catch the little one when she bolted away. Of course there is a flip side to every situation, and that was just one person.

Anyway, about the picture: Harry is just ADORABLE!!!

janeen on

Everyone is discussing the age of nannies and stuff and I am just wondering why they would need a nanny on vacation for just one child. I would think they would want time alone from everybody and just be with the immediate family unit. Well maybe that is just me 🙂

monica on

Great place to go!!
looks like fun!

EnoughSaid on

Did any of you actually read this article? They clearly state his girlfriend is not pictured.

Anonymous on

this is from 2008! I knew Harry was older than four. Why was this even a news story? It’s old.