Youth Is Fleeing

My friend is constantly dragging me to parties to be her wing woman. She's in her late 40s but hits on hot young guys in their early 20s who never reciprocate interest. Guys her age or older approach her, but she blows them off. I'm sick of these depressing evenings and of accompanying her to the mall so she can get "hipper clothes." Is there a kind way to tell her she needs to rethink who she's pursuing?

--Frustrated

How uplifting, spending your weekends watching Generation Y getting hit on by Generation Why Are You At This Party? Of course you want to clue in your friend, "You could wear head-to-toe Forever 21, and you'd still look 49 and counting." And you could gently suggest she expand her dating horizons to include men who are actual possibilities. But her persistence in the face of failure suggests she's pretty attached to believing that the answer to her datelessness can be found at the mall. What you can control is how you spend your time. Extending yourself to make a friend happy is nice; subjecting yourself to regular misery is too nice and leads to bubbling resentment. The next time she tries to drag you along, tell her you're party-weary and tired of the mall...but how about lunch or a hike? Granted, out on the trail, you could still witness the uncomfortable sight of a cougar stalking its prey -- but not by changing out of its mom jeans.