Dear Anna,

I’ve been with my girlfriend for about a year. Things have been great overall. But lately she’s become fixated on one of her close friends, not in a romantic way — more in a spiral of comparison. Her friend is pretty, but so is my girlfriend, except when she makes self-deprecating comments about how she “could never compete” and “no wonder people always notice her first.” I’ve done my best to reassure her, but nothing I say seems to land.

Then something really strange happened. A few weeks ago, I got a flirty DM from this friend — nothing explicit, but enough to raise an eyebrow. When I mentioned it to my girlfriend, she admitted she’d asked her friend to send it as a “test” to see how I’d respond. She said she needed to “prove” to herself that I wouldn’t take the bait. I didn’t, obviously, but I was shocked and hurt. It feels humiliating that she didn’t trust me enough to just talk to me, and even more uncomfortable that she dragged someone else into it. When I tried to tell her that it upset me, she got defensive and said she “just needed reassurance” and that I was “taking it too seriously.”

I love her, but this crossed a line for me. I’m questioning whether I can trust someone who tests me like that, but I also don’t want to shame her or make her feel worse about her insecurities. Is this a red flag I shouldn’t ignore? — Tested And Tired

Dear TAT,

You’re not wrong to feel shaken. What your girlfriend did wasn’t just “a loyalty test” — it was a mind game and an act of emotional sabotage, born from insecurity but carried out in a way that undermines trust. It’s one of those f—ups that reveals how wide the gap can be between loving someone and being able to build something lasting with them.

Let’s start with empathy, though, because it’s clear she’s spiraling if she was low enough to do something like this. You describe your girlfriend as caught in the exhausting loop of comparison — looking at her friend, then back at herself, and always coming up short. That’s not rational jealousy; that’s self-loathing disguised as vigilance. She doesn’t actually think you’re attracted to her friend — her friend doesn’t matter in the slightest. This is about her relationship with her own self-worth.

When people live inside their fear and insecurity long enough, they sometimes stage situations that force proof. “See,” they tell themselves, “now I know I can trust him.” But the proof never lasts. It’s like drinking salt water to quench thirst.

And unfortunately, in trying to soothe her insecurity, she disrespected you big time. She didn’t just doubt your loyalty; she manipulated a situation to test it, pulling another person into your relationship like a prop. That’s not harmless curiosity — it’s a breach of trust, even if she meant it as reassurance.

You asked how to tell her she hurt you without making her upset. The short answer is: You probably can’t. Firstly, because you’re not responsible for her feelings — only she is. And secondly, people who act from insecurity often react to confrontation as further evidence of rejection. But you can frame the conversation in a way that hopefully invites reflection rather than escalation.

Try something like:

“I love you, and I understand that you’ve been feeling insecure — but when you involved your friend to ‘test’ me, it made me feel humiliated and distrusted. I didn’t fail your test, but it still felt like being punished. I need us to find ways to build trust through communicating, not experiments.”

This does two important things: It names your emotional reality and separates your empathy for her feelings from your boundaries. You’re saying, “I see your pain, but you don’t get to wound me to measure it.”

If she can meet you there — if she can listen, take responsibility, and talk honestly about what’s driving her insecurity (preferably with a therapist) — then there might be room to rebuild from here.

If, however, she dismisses your hurt or insists you’re “overreacting,” that’s a different kind of information. It tells you that the next test won’t come through her friend’s DMs, but through subtler means: guilt, suspicion, withdrawal.

You can love someone deeply and still recognize that their fear of being abandoned is pushing you away. That’s the tragic symmetry of insecurity — it builds the very distance it’s trying to prevent.

Good luck, TAT. You can’t fix her self-image, but you can draw the line when it comes to your dignity.

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