Dear Bess,

I’m 64, recently widowed, and about to go on my first date in nearly forty years. My daughter has been helping me set up a dating profile, which has been an education in itself, but the thing that’s actually keeping me up at night is far more basic than any app. Do I still open the car door for her? Do I pull out her chair? I don’t want to seem old-fashioned, but I also don’t want to seem like I don’t have any manners. Nobody tells you the rules have changed. What am I actually meant to do?

Signed, Rusty at the Kerb

Rusty, I want to start by telling you something I think you already half know but haven’t quite let yourself believe: the fact that you’re asking this question at all tells me you’re going to be perfectly fine out there. The men who cause genuine trouble on dates are never the ones lying awake wondering if they’ve got the etiquette right. So take a breath. You’re one of the good ones, worrying about exactly the right thing.

Now, to your actual question. Open the door.

I want to be direct about this, because I think men of our generation have been handed a genuinely confusing message over the past few decades, and it’s led a lot of good men to freeze up entirely rather than risk getting it wrong. Here’s the truth as I understand it, having spoken to a good number of women navigating exactly this same re-entry into dating: nobody is offended by a man opening a car door or pulling out a chair. What women are tired of is a man who performs those gestures like a transaction, expecting something in return for them. The gesture itself was never really the problem. The entitlement sometimes attached to it was.

So open the door, genuinely, warmly, without ceremony, and then get on with having a nice evening. If she’d rather open her own door, she’ll simply do it, and no harm will come to either of you. Chivalry hasn’t died. It’s just stopped being compulsory, which, if you think about it, makes offering it mean rather more than it used to, not less.

The bit nobody warns you about: the new language

Here’s where I suspect your daughter has already started translating for you, and where I think a proper glossary will save you a great deal of confusion. Dating in 2026 comes with its own vocabulary, and while you don’t need to memorise all of it, a handful of terms are genuinely worth knowing, because the behaviours they describe are things you’re likely to actually encounter.

Ghosting is when someone simply stops replying to messages entirely, with no explanation, rather than telling you plainly they’re not interested. It’s rude, it’s common, and it says considerably more about the person doing it than it does about you.

Breadcrumbing is when someone keeps sending you just enough attention, an occasional message, a like on a photo, to keep you interested, without any real intention of actually meeting up or committing to anything. If you notice a lot of flirty texting and very few actual plans, that’s your answer.

A situationship describes a relationship that’s clearly more than casual but has never been properly defined or discussed by either person. If you find yourself several months into something that feels like a relationship but has never actually been named as one, it may be worth having what’s now called a DTR conversation, which simply means sitting down and plainly asking where things stand. I’d argue this is just good, honest communication with a trendy new label, and I heartily approve of it either way.

Love bombing is when someone comes on remarkably strong, remarkably fast, big compliments, grand gestures, talk of the future within the first few weeks. It can feel flattering, but it’s genuinely worth treating with a little healthy caution rather than being swept away by it.

None of this is as complicated as it first appears. Underneath the new vocabulary, it’s the same handful of human behaviours people have been navigating in dating for as long as dating has existed. The words are just catchier now.

What I actually want you to know, Rusty

Coming back to dating after loss, whether through death or divorce, at our age is a genuinely brave thing to do, and I don’t think that gets said to men often enough. You’re not required to be smooth. You’re not required to know every piece of slang your daughter throws at you. You’re allowed to say, plainly and without embarrassment, “I haven’t done this in a long time, so bear with me.” Most women your age will find that considerably more endearing than a man pretending he’s got it all figured out.

Open the door. Be honest when you’re nervous. Ask questions and actually listen to the answers. And if someone breadcrumbs you, zombies back into your life after weeks of silence, or leaves you sitting in a situationship with no clear label, you now know exactly what to call it, and exactly that you deserve better than it.

Good luck out there. I mean that sincerely.

Have a question for Bess? Write to her at community@startsat60.com with “Dear Bess” in the subject line.