Robin in Latham writes:
My boyfriend and I have been dating for about 4 months and I think he's hysterical but sometimes the way he jokes with people rubs them the wrong way.  He doesn't do it on purpose, but his sarcastic nature makes some people feel uncomfortable.  He upset my sister and her husband recently by cracking a joke about their dog- a rescue. This was the first time they met him and he asked if the dog looked cuter 3 years ago, to which they replied - she's only 2.   Then he said 'Exactly!" 
Needles to say, the wise crack didn't go over too well and I've asked him apologize, but he's says they need to lighten up.  Please help
Love Cowboy knows a thing or two about busting chops but did Robin's boyfriend go over the line here?

Love him or hate him, the Love Cowboy is about as consistent as they come. Every weekday morning just after 6AM and 8AM, he saddles on up inside the GNA studio. He comes with relationship advice for you GNA listeners and insults for anyone who dares to get in his way; usually, that person is Brian.Overall, it's his no-nonsense approach to life, love, and the current state of affairs that make him quite refreshing in today's climate. Be sure to check out the replay of each daily segment, the next morning just after 6AM.If you have a question for the LC, hit us up at mornings @wgna.com

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