The rules for planning a date

Yep. If a guy makes no effort to get you, you are not his "No. 1 pick".

Same with writing you and kinda expecting you to start a decent conversation.

I'm a late-30s dinosaur and first started online dating in 2009. Men on OLD back then were downright genteel compared to the men on OLD today.

Almost every man who messaged me wrote thoughtful, interesting conversation starters. They introduced themselves, asked me polite questions about myself, and sprinkled a little humor on top. These messages were two or three short paragraphs long and felt natural and conversational.

Back then, nobody was expected to respond to a message within 24 hours. I think the polite amount of time between messages was 2-3 days. Even a full week was OK, as nobody was expected to check their dating apps more often than 2-3 times a week. There was never any double-messaging. So if a man wrote me, I responded after 2-3 days, he responded after 2-3 days, and I responded after 2-3 days, and so on, it would feel natural for the man to ask me out after 2 weeks. Fewer than 2 weeks was suspect. Much more than 2 weeks was also suspect.

Exchanges never felt rushed, and over two weeks of thoughtful messages (each about 2-3 paragraphs in length), the men and I got to know each other a little bit--enough to know if we wanted to meet for dinner, but not enough to kill the mystery.

The point of my story is that a man asking you out should never feel rushed or delayed. I would never respond to a man's message within 24 hours and would not expect him to respond within 24 hours. We're supposed to have a life outside dating apps, and it won't seem like you have a life if you're checking your OLD apps multiple times a day.

I realize OLD in 2025 is not OLD in 2009, but those are my two cents.

I feel like it depends how much you’ve talked, but if you are a conversational point where you feel comfortable meeting in person, and/or it has been suggested that you meet.. I give 48hrs before a solid plan has been made. That’s plenty of time for them to come up with and plan a nice date for the two of you. If you haven’t heard back by then, they’re not into you enough. It honestly doesn’t matter at that point whether he’s into you or not, only that he’s not into you enough for you to want to meet him. Any man who is into you enough will be going out of his way to plan something great, and he’ll be in communication about it in the meantime.

I like to chat for a couple of days, up to a week before arranging to meet. I see what you’re saying about disinterest, but I’ve also encountered the opposite where men who are too eager are desperate af and there’s usually something wrong with them. It’s about balance and using your best discretion.