Holiday Sparks, Work Wives and Cloud Backups: Jana Hocking’s Advice on Modern Relationships

Three reader questions to Jana Hocking’s ASK JANA column illustrate how modern relationships face emotional gaps during travel, in workplace chatter about sex, and in the lingering archive of dating-app pasts stored in the cloud.

Sunset Confessional details a wife who attended a destination wedding without her husband because he could not take time off. On the second night, after margaritas and a sunset swim, she spoke at length with the groom’s best man. They held hands, and at one point he kissed her forehead and said, "I’ve wanted to do that for years." They did nothing physical, but she returned home shaken and questioning whether she had been emotionally starved at home. Hocking counsels that the romance felt heightened by the exotic setting and the moment, not because the other man is a soulmate but because he arrived at a time when she was vulnerable and out of routine. "Everything seems far more romantic in an exotic setting," she writes, emphasizing that the moment was a contrast rather than a destined union. The takeaway is simple: talk with her husband about emotional presence, and consider reconnecting—perhaps with a weekend away—rather than turning the incident into a referendum on the marriage.

Back-up Plan Girlfriend centers on a partner who keeps a folder titled "backup" in the cloud, containing screenshots of dating profiles, conversations with women he matched with before they met, and notes about what he liked and didn’t like about them. He swears the profile isn’t active and that he isn’t cheating, even presenting metadata that supposedly proves the screenshots are old. The mere existence of such a repository, however, makes the reader feel disposable and unsettled. Jana calls this type of digital clutter creepy but not automatically evidence of an affair. A key concern for the reader is the word "backup" itself, which implies a hypothetical replacement or insurance policy. The recommended course is a calm, direct conversation: ask why the folder exists, what it signals about his sense of security, and whether he would delete it if asked. If he deletes it and explains his motives without defensiveness, the reader can view it as a misstep that’s been corrected. If defense or minimization follows, it becomes a potential warning sign to monitor more closely. The core message is that emotional safety matters more than the mere presence of old dating content, and both partners should feel valued and chosen in the relationship.

Dear Jana, I have a good girlfriend who works for the same company as my husband, but in different departments. While at dinner last week, she pulled me aside and said she overheard my husband discussing our sex life with another female coworker—someone we’ve always jokingly called his 'work wife.' Apparently, they were in a group talking about how often they have sex—and my husband said something to the effect of, "I get it once a week—twice if I’m lucky." I know he didn’t mean to disrespect me, but I feel so uncomfortable about him sharing that information. I confronted him, and he said it slipped out because she’s “easy to talk to.” He stressed that she’s married too, and he’s not even attracted to her. Still, something about this unnerves me. I don’t want to be controlling, but I also don’t love that another woman knows how often we have sex. Should I let this go?

Work Wife Widow translates this into a broader workplace dynamic, noting that while men often vent about marriages in casual settings, intimate details can feel invasive when shared with a coworker. The term 'work wife' itself can sting for a real spouse. Jana observes that, in many cases, the sharing reflects normal, if unfiltered, male banter, but the real issue is boundaries and respect. The suggested first move is to assess whether your husband truly understands why this bothers you. If he acknowledges the line was crossed and commits to avoiding similar disclosures, the matter may be navigated without ending the relationship. If he minimizes it or treats your concern as overreaction, that warrants closer attention. The advice is clear: reduce the volume on outside confirmation of private matters and invest in direct, honest conversations about what you both consider acceptable to share beyond the couple.

Taken together, the letters illuminate a broader trend in culture and entertainment reporting: advice columns increasingly address the emotional labor of relationships in a connected, fast-moving world. The destination-wedding vignette underscores how travel moments can feel sensational but are rarely determinative of long-term fidelity. The cloud-folder scenario spotlights the paradox of digital memory—past dating prospects linger in the ether, even when not actively pursued. And the work-place exchange demonstrates how public professional spaces can intersect with private life in uncomfortable ways when intimate details slip into conversations outside the marriage.

In each case, Jana Hocking’s guidance centers on communication, self-reflection and boundaries: acknowledge what’s missing without turning a single moment into a verdict on the entire relationship; name what is and isn’t acceptable to share with others; and, when in doubt, reconnect with the partner through calm dialogue or a planned, intentional moment away to restore emotional closeness. While the specifics differ—from a sunset kiss to a cloud folder to coworkers at a dinner table—the underlying principle remains consistent: trust is sustained by clarity, not by silence, and relationships endure through ongoing, respectful conversations about needs, boundaries, and what counts as intimacy in the digital age.