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There was a rumor started on a message board many months ago that Gary was seen around his town with his pregnant girlfriend. There is nothing that confirms this though. I don't believe that he is engaged, but he was (is) living with Jessica Shafer. If you go to Country Weekly there is a picture of them if you search for Gary Allan and date (BMI awards 11/10/10). If you go to her myspace page there are also pictures of his dog Lucy on her page. However there is another girl named Dusty that popped up around the same time who a few other fans have met out and about (in Rockford, NC, Chicago, and WI). She has firmly denied that they are in any form of a relationship and her facebook profile has her in a relationship with another man. When some of us have met her either at a show or in the hotel after she was just a bubbly sociable girl who seemed comfortable talking to anybody. She never brought him up, but when asked she did say she knew him. She was seen getting on the bus after several shows escorted by either Levi or Jamie.
So my answer to this question is I don't believe that Gary Allan is even engaged at this time. I believe that he is friends with Dusty and in a serious relationship with Jessica Shafer. If you ever meet Dusty she comes off as a "guys girl, buddy buddy" and Jessica looks more like the sexy wife at home. that is a compliment to both girls by the way.
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try going to google and look for a box titled images and click it and type Gary Allans girlfriend.
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