My first thought: I wonder if the wife/gf will be able to tell that the gifts aren't personal.

My second thought: What if they find out? Suddenly the BF/husband would go from being "TIMELY, THOUGHTFUL, AND INTENTIONAL" to "cold, careless, selfish bastard who thought he could fool me and take credit for some automated gift system."

I am by no means trying to shoot down the idea. I just thought since I am (presumably) part of your target audience, you would be interested in my first impression and concerns.

I am not sure if that is relevant that the gifts are from an automated service. Surely the husband was thoughtful in choosing and signing up for the gift service in the first place?

I think the point of giving a small gift that isn't tied to a holiday or event is to show that:

a) You were listening to her when she mentioned last week how much she loved $thingX, and

b) You took the time out of your busy day to get her something nice.

Using an automated service doesn't meet either of these, which is why I think it takes all the charm out of it. Maybe I'm wrong and they spoke with 50 customers who love this, but that's just my feeling.

Hey men, OP here. Thanks so much for the feedback, we are really looking for honest feedback from guys like you.

Yes the wife finding out is a consideration. What has been weird though, is the wives we've talked to love the idea. A random gift is better than no gift at all, I guess. My first thought is ask your wife what she thinks about it.

We are looking into customizing the experience later down the road, but up front we hope to take the hard part out of giving gifts, followed up by making the gift experience better and better.