While I respect the opinion of every one saying to take your wife along with you on the first ride, I'm not so sure that it would have the desired effect.
If she freaked when crossing the road the last time, she's likely to freak even more when you're there with your child.
Obviously she sees danger in a situation that you don't. She'll still see that danger if she's there when you're crossing with the trailer. Probably even more so.
Always remember that you're on the same side. You're both trying to provide what is best for your family - you just have different opinions on how to achieve that result.
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