There is an element of Respectful Requests when negotiating where you can agree to give things a try for a little while and re-evaluate. I have my books packed up right now so I'm going off of memory.

In the example Dr. Harley discusses seatbelts where one spouse hates wearing them but the other respectfully requests that they do wear it. The agree to have the spouse who isn't into seatbelts try wearing one for 3 months then they re-evaluate.

Sometimes when we're POJAing something, either I or my husband may be iffy on our level of enthusiasm, but we agree to go ahead with what we've decided. Sometimes the hesitant one becomes enthusiastic and sometimes they find out they aren't. Either way is a win, because now you have more information with which to make a decision.

So would your wife be willing to try the babysitting date-night at least once a week (or heck twice if she's willing to try that) for say a month or two and see if her reservations or worries diminish over time?

If they do - then you're set. If they don't then it is likely that the process will reveal to her what exactly the problem is so that you will be better equipped to overcome it.

Leaving your baby the first time is rough... over time it can get better.