Dating Advice w/Heather: Age Is A Number Edition


Heather is a single female comic in her late 30’s who has been on 22 dates in the past eight months and still lives alone with her cat.

Heather Kozlakowski


Letting her give dating advice is absurd.

Dear Heather,

I’m almost 40 and my man is almost 50; I think he is HOT AS HELL! He, on the other hand, is really embarrassed; he lies about his age and has a tendency to act…less than age appropriate. How do I get him to accept reality and love himself as much as I love him?

My Old Man is HOT

Dear My Old Man is HOT,

I’m super curious as to what “age appropriate” might be? Is there an Ice Luge in the kitchen next to his Arthritis Medication? Leave him alone, keep telling him he’s “HOT AS HELL” that’s YOUR JOB; HIS JOB is to learn how to love himself.

Dear Heather,

I met this sweet, sweet man, he is 20 and I am almost 40. What do I do? He’s only a few years older than my best friend’s SON! Can I really do this?

Robin Cradle

Dear Robin Cradle,

Um, NO. Do not pass go. The “man” can’t even buy you a 40oz of Malt Liquor! As they say, “If you love something…let it GROW UP!”

Dear Heather,

I’ve been dating this woman for 40 days now and, I’m embarrassed to say, we have not had sex yet. I’m trying to be a gentleman, but I’m starting to feel like she isn’t even interested. What should I do?


Dear Noah,

When courting a woman you might want to follow the “40 Days and 40 Nights Rule” If things haven’t gotten wet and sticky by then, the situation has dried up and you need to move on. I suggest you treat yourself to a nice meal, possibly at the Olive Garden, maybe have a Dove Bar for desert?
In fact, have two, you’ve earned it.

Got a question for Heather? Tweet her at @Hkozlakowski

Check out all of Heather’s Dating Advice Columns

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