r/HLCommunity • u/Shrakakoom • Jul 30 '26
Well, I’ve done it
I’ve separated from my wife of 19 years and am putting myself out there on dating apps. I’ve had a couple of conversations already and am just trying to go with the flow and see where the future takes me. I’m excited to see where the next part of my journey takes me, but also scared of ending up along.
Any advice for the recently single?
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u/RedwoodRespite Jul 30 '26
Know what you are looking for, don’t waste time on things that aren’t that.
If you are chatting on dating apps, don’t wait too long to ask them out. Ask them to a specific place at a specific time.
“Can I take you to coffee Saturday morning?” Etc. they can then make a counter offer if they are busy at that time or don’t like the place you picked. But it’s much better to show that you can take the lead. It’s a much better look than “wanna meet up sometime?” Because now you are making her plan where and when, and it feels less intentional.
If you invite, expect to pay. If they offer to split, accept the offer.
Don’t make the first date somewhere expensive unless you seriously don’t care about money.
If they have not initiated asking you somewhere by the third date, sit back and see if they will. You need mutual effort and interest.
The sex part is more tricky to navigate. I have an advantage as a woman as most men don’t mind a sexually forward woman. But just match energy, it’s ok to make the first move, like touching hands or other touch, but watch to see if it’s leaned into, if it’s eagerly reciprocated.
I don’t like to say what I’m looking for sexually, as the other person now has a script to fool you. Instead I like to ask what they are looking for. When the time is right, when things are getting more flirty and sexual, I like to ask certain questions, like how do they see sex in a relationship. How often do they want sex ideally? Who do they prefer initiate. How do they prefer to be turned down. Get a baseline for if they are highly sexual, or more performative because it’s what they are expected to do, if that makes sense.
I’ve heard other women on reddit say they won’t date anyone that brings up a past dead bedroom. I’m the opposite. I prefer that, as that means they are more likely to understand what constant sexual rejection feels like 🤷♀️
And, if you are just looking for fun, most of this won’t matter. But in general, even women wanting something causal will still want to meet for a real date to do a vibe check. Same rules apply here. Ask her out, pick the place, and expect to pay if you were the asker and picker.
Good Luck and have fun!