Jessa has been dating a guy named Ben Seewald. The family has been very open about the fact that they were in a courtship, but during a courtship you are only supposed to date in a group setting so that doesn't explain why there are a ton of pictures out there of them alone. They should only be allowed to be alone if they have moved into an engagement.
One other thing that is going on is that there are some pictures of Jessa and Ben that are obviously done by a professional photographer. That makes it very possible that they were actually engagement photos but of course her ring finger isn't being shown at all in the pictures.
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