Dear Anna,

I’ve been messaging someone I met on a dating app for about three weeks, and we finally have our first date this weekend. We’ve had some really fun conversations, and I’m genuinely excited to meet her. The other night she mentioned that she’d been reading a book she loved, but her library hold expired before she could finish it and now there’s a long waitlist. It got me thinking about buying her a copy as a little surprise to bring on our date. Part of me thinks it’s a thoughtful gesture. Another part of me worries it might come across as love bombing, especially since we haven’t met in person. I definitely don’t want to make her feel like she owes me anything. Is this sweet, or should I save the grand gestures for later? — Trying to Get It Right

Dear TTGIR,

I don’t think it’s love bombing at all.

Love bombing isn’t about doing something nice once. It’s about using affection as a way to create obligation, dependency or emotional acceleration.

You’re not trying to convince her you’re soulmates. You’re demonstrating that you listened.

That said, context matters. A modest paperback with a simple, “You mentioned this, and I thought you’d enjoy finishing it,” lands very differently than, like, an expensive, signed, first-edition copy with an inscription about how your fates are bound like the pages of this book.

The other thing I’d check in with is your motivation. Are you giving her the book because it would genuinely make you happy to do something kind? Or are you hoping it’ll help you stand out, guarantee a second date or prove you’re “different from other guys”?

The first is generosity. The second is expectation wearing a nice outfit.

Personally, I’d find the book charming. It says, “I paid attention,” which is one of the nicest things you can communicate on a first date. Just give it lightly. No fanfare, no pressure and no expectation that it earns you anything.

Dear Anna,

I have two close friends who have never met, and I can’t shake the feeling that they’d absolutely hit it off. They’re both single, queer, have eerily similar senses of humor, love the same weirdly specific hobbies, and every time one of them tells me a story, I think, “Oh my God, the other one would love this person.” The problem is that neither of them has asked me to play matchmaker. I don’t want to make either of them feel like I’m trying to manage their love life or imply they should date just because they’re single and I’d like them to. On the other hand, if I did nothing and they ended up being perfect for each other, I’d kick myself. Is there a tactful way to set two people up without making it weird? Or is this one of those situations where I should keep my mouth shut? — Cupid, A Love Match?

Dear CALM,

I’m generally pro-setting-people-up, but with one important caveat: You can make an introduction. You can’t write their story.

Where people get into trouble is when they become emotionally invested in the outcome. Suddenly every text message is analyzed, every scheduling conflict is a crisis, and a coffee date has somehow become a referendum on your judgment. That’s too much pressure for everyone involved.

Before you do anything, ask yourself one question: Would I still want these two people to meet if romance were completely off the table?

If the answer is yes, you’re in good shape. That usually means you’re responding to genuine compatibility rather than trying to solve two people’s singleness with one convenient solution.

The most tactful approach is also the simplest. Reach out to each person separately and say something like, “This might be totally off base, but I know someone I think you’d genuinely enjoy meeting. No pressure at all — would you be open to an introduction?”

What not to say: “You’d be perfect together.” Or “I just know you’re going to love them.” Don’t treat them like two puzzle pieces you’ve already decided belong together.

And if either person says no, that’s the end of it. No convincing, no “just trust me,” no asking why. Compatibility isn’t about whether you think two people would get along; it’s also about whether they’re open to meeting someone new in the first place.

One last thing. Don’t confuse compatibility with chemistry. You might be spectacular at spotting shared values, complementary personalities and mutual interests. You are much less qualified to predict whether two people will actually want to make out.

You can, however, open the door.

Whether anyone walks through it is happily out of your hands.

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