Headphone/handsfree annoyance

Blackberry Curve 3G 9300, software is OS 5
I have a wired headset that works just fine, but I'm very annoyed that after answering the call, I have to press the speaker/$ button to activate it. This is quite frankly a pain in the tush.
Is there some sort of preferences that I have missed that will make the BB route the call to the headset automatically when it is plugged in?
The BB seems very capable of routing the call to my bluetooth Garmin in the car.
TIA

You can try searching for a 3.5mm headset that suits you at RadioShack.
Ron
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