scorecardresearch Skip to main content

A friend asked me out on a date, but I’m not sure I should accept

Her overly critical opinions on dating give me pause.

Love Letters

Q. Recently, Ann (30s), a friend, asked me out on a date.

She has never dated or been in a relationship, and takes an idealistic, hard-line stance when it comes to how people in relationships should behave.

She judges our friends’ relationships harshly, and her default advice is “break up.” Is this a result of having no relationship experience? Will this relax as she gains more experience? I am inclined to turn her down, but don’t know if I am being too hasty. She is a good friend in other aspects.

– Astronomical Standards

A. If you’re into Ann, have thought about kissing her, and suspect you could have fun being alone with her, say yes to the date.


Sure, it’s a risk to the friendship — and maybe the friend group — but that’s part of the dating experience. A date can wind up being awkward and weird, but there’s also the potential for it to become something wonderful.

Maybe you’re feeling indifferent about Ann’s interest, but the fact that you wrote this letter tells me you’re curious, at the very least.

The thing to consider about her judgment — and “just break up” advice — is that it’s very easy to tell other people what to do while watching from the sidelines. Trust me, I do that every day. Ann might have a different attitude about her own relationships. She might learn a lot by becoming the main character in a love story.

Sometimes, when I’ve been single for a long time, I decide that my friends’ relationships should be perfect for them, in all ways. Then I remember that our own friendships aren’t perfect. We’re always making mistakes, learning, evolving, etc. Ann could figure out that even the best romantic partnerships are messy — because we’re all adjusting as we go.


We don’t know what Ann wants or how she’ll behave, so this really comes down to your desires. Again, I suspect you want to try this — for a date, at least. If not, that’s fine too. But I assume you wrote this letter for a reason.

— Meredith


Ask yourself: “Do I like Ann enough to date her and have a different type of relationship?” Seriously think about it. No sense wasting time if you aren’t really into her. MHOUSTON01

Ann is probably going to get a little impatient when you keep her in suspense while you wait for the verdict of the commentariat. CANNONFODDER22

If I were you, I would steer clear and realize this may be more mess than it’s worth. Just find a woman whose outlook you admire more. LITTLEPENGUIN456

If you want to turn her down, it should be because you don’t like her in a romantic/dating way. The only question you should be asking yourself is, “Do I like Ann?” If you decline, be kind and leave your judgments of her judgments out of it. SURFERROSA

You mentioned more of what you didn’t agree with vs. did agree. Politely and kindly decline. NANOSECO

Open the tab and fill out the form and hit submit. That's it! Keep a look out for your question in the next Love Letters.