Dear Anna,

I've been dating my boyfriend (36M) for five months, and recently, I found out that he had quite a reputation for sending unsolicited, borderline harassy messages to women online. A coworker of mine showed me some of his old DMs on Instagram — telling her how hot she was, and asking her out repeatedly, even though she never replied, and so on. He even messaged some of her friends the same way, often without any replies.

To be fair, this was before we got together, and from what I know, he hasn’t done it since. But here’s my issue: Reading those messages now, I can’t help but feel a little gross. He put so much effort into messaging these women, giving them compliments, and asking them out over and over again. But with me, he rarely compliments me, hardly puts effort into planning dates, and feels distant. It’s like he worked harder to get the attention of random people than he does to nurture what we have now.

I know the past is the past, but I’m struggling with some resentment. I can't stop comparing the energy he put into chasing these other women with how he shows up (or doesn’t) in our relationship. Any advice on how to move past this? — DM Drama

Dear DMD,

Finding out that your partner once poured time and attention into DMing other women — especially one-sided messages that read as creepy/harrassy — can stir up feelings of hurt, confusion and cringe, maybe even a sense of betrayal, even if it was before you were together. Couple that with the fact that he’s phoning it in with your relationship — and only five months in! — is troubling indeed.

First off, it’s natural to feel disappointed and unsettled by this. It’s not a good look. Plus, relationships thrive on respect and mutual effort, and seeing a side of your boyfriend that feels inconsistent with the energy he’s putting into your relationship now can make you feel like something is lacking. What you’re dealing with here is a mix of two things: the past version of him that acted impulsively to grab attention and/or dates, and the current version who seems not very invested in your relationship. The key is to understand why this change might have occurred and to find ways to communicate what you need going forward. (And if that fails, then to move on.)

An initial step is to have an open, compassionate conversation with him about this. Bring up your feelings without framing it as an accusation. You might say, “When I saw those old messages, I felt confused. It seems like you were putting so much energy into pursuing attention from people who weren’t even engaging back. And now, in our relationship, I sometimes feel a lack of that same enthusiasm and effort.” This can open a door for him to explain where he’s coming from. It’s possible he’s not fully aware of the differences in his behavior, or he may have consciously shifted his approach, thinking this was what a “mature” relationship looks like.

Next, figure out what “effort” means to you and communicate those needs as best as you can. For some people, it’s compliments and quality time; for others, it’s planned dates or small acts of thoughtfulness. Instead of focusing on what he used to do (if he, indeed, did these things before), try sharing specific ways he can make you feel valued now. “It would mean a lot to me if you planned an evening together once a month” or “I love hearing words of appreciation — it helps me feel connected.” Being straightforward about what fulfills you can guide him in showing up for you in a meaningful way.

It’s also helpful to examine your expectations about his past. Everyone has some behaviors we regret or ways we’ve evolved over time. By acknowledging this, you’re allowing room for him to be human and for your relationship to develop on the foundation of who he is now, rather than past actions. As difficult as it may feel, try to separate who he was in those DMs from who he is today.

Lastly, remember that energy in a relationship is a two-way street, and it’s good to check in with your own sense of fulfillment, too. Keep asking yourself if he’s meeting your core needs now. If, after openly communicating and giving things a bit of time, you still feel like he’s holding back or doesn’t value the relationship enough to reciprocate, that might be a sign to reassess your connection.

As the poet Rumi said, “Seek the wisdom that will untie your knot.” Your instincts and emotions here are part of that wisdom. If you approach this with curiosity, compassion and self-respect, you’ll either find a way to grow together or gain clarity on what’s truly best for you and find someone better suited.

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