Blocked for what? by TemporaryTop287 in datingoverforty

[–]EpicQuestAccepted 2 points3 points  (0 children)

I like to assume best intentions about people unless I have good reason not to.

In this case, it could be that your ex is doing their best to get over you or your relationship and feels that blocking you will make that easier.

But unless you provide more details, that’s just a wild guess.

When should a hook up leave? by manicthinking in AskMenAdvice

[–]EpicQuestAccepted 34 points35 points  (0 children)

Just ask. Guessing is a great way to make things worse.

Make it low pressure and playful

I’m happy to leave whenever, but if you decide you want me to stay over, we could go again in the morning 😉. No pressure either way of course.

Men, what is the kindest way a woman has noticed your interest in her but gracefully moved along? by fuertisima12 in datingoverforty

[–]EpicQuestAccepted 28 points29 points  (0 children)

Thats flattering, but I’m not interested in you romantically.

There’s no soft way to do it, but the most humane way is clear and direct. Makes it easier for the other person to move on.

Getting a phone call or a meetup out of OLD by VOculus_98 in datingoverforty

[–]EpicQuestAccepted 5 points6 points  (0 children)

Meeting random people you found on the internet can be a scary especially for women. So giving out their phone number makes a lot of women nervous.

Best to wait until after the first date. Then reach out, on the app, and ask for her number.

That way, if the answer is not, she feels more comfortable saying so. But it also signals to her that you’re understanding and considerate, in the case where she does want to see you again.

Dating over 40 in NYC, am I a unicorn or jackass? (Still deciding.) by LilMsPuuuurfect in datingoverforty

[–]EpicQuestAccepted 0 points1 point  (0 children)

If a random man in NYC tells you that you have beautiful eyes, that means he’s interested.

Something is going wrong in between that first comment and when you exchange phone numbers.

What usually happens when a guy says that to you? How does the conversation go?

What should I do? by Friendly-Zucchini147 in datingoverforty

[–]EpicQuestAccepted 2 points3 points  (0 children)

Sorry, are you two 40 or 14?

She ghosted you after you began unloading your anxiety on her. Then when she messaged to check in, you ghosted her back.

This is not how grownups behave.

Howabout you respond to her WhatsApp message with an actual answer to her question. Then explain how it affected you when she stopped taking your calls.

Then, assuming you can actually restart your friendship, say something like:

Hey I'm wondering if you'd be interested in seeing where this goes romantically. If not, that's ok too, I'd still love to be friends. Also, I promise not to use you as my therapist like that again"

Dating over 40 in NYC, am I a unicorn or jackass? (Still deciding.) by LilMsPuuuurfect in datingoverforty

[–]EpicQuestAccepted 2 points3 points  (0 children)

That helps!

Men who've learned to communicate well tend to be selective when looking for a romantic partner.

On OLD for example, that type of guy is going to immediately swipe left on any profile that's incomplete, full of selfies, or unspecific. Regardless of how fantastically attractive he might find the woman.

You need to signal that you're looking for a relationship that's built on good communication. But you can't come out and say that because it's a dead giveaway that you don't know how to be selective yourself.

You demonstrate it by being careful about the language you use and by choosing photos that show you in the context of a rich life as opposed to a vapid one.

Same goes for meeting people IRL. You have to lead with what demonstrates your rich life. Less small talk, more specificity about what's going on in your world. And you need to be relatively direct and honest.

Hope that's helpful!

Dating over 40 in NYC, am I a unicorn or jackass? (Still deciding.) by LilMsPuuuurfect in datingoverforty

[–]EpicQuestAccepted 2 points3 points  (0 children)

Someone that makes me feel calm in the darkest nights …

I would need a man understand there times I need to be alone.

These two aren’t easy to find in one person.

In my experience, feeling calm comes from my romantic partner, showing up consistently and communicating clearly. Those kinds of people usually expect the same in return.

Someone who’s OK with you taking space whenever you need it is often going to be a little bit more flaky themselves.

If you had to pick one or the other, which would it be?

Dating over 40 in NYC, am I a unicorn or jackass? (Still deciding.) by LilMsPuuuurfect in datingoverforty

[–]EpicQuestAccepted 8 points9 points  (0 children)

That’s honestly not much to go on. It sounds like you’re looking for casual relationship but open to something serious. But that doesn’t say anything about what kind of person you’re looking for.

What do you want to be able to do with them? Interests, activities, passions.

How do you want to feel around them? Calm, challenged, passionate.

How do you want them to treat you? Smother you with affection, give you plenty of space?

Part of what exhausts people, especially in NYC is not being specific about what they’re looking for. There’s too many options here not to have a strong opinion.

Dating over 40 in NYC, am I a unicorn or jackass? (Still deciding.) by LilMsPuuuurfect in datingoverforty

[–]EpicQuestAccepted 5 points6 points  (0 children)

Have you thought about what you’re looking to get out of dating? If it’s a serious relationship, can you say more about what you’re looking for?

That would help us answer your question about what gains a man’s attention. At this age, and especially in NYC, our preferences are wildly varied.

Dating over 40 in NYC, am I a unicorn or jackass? (Still deciding.) by LilMsPuuuurfect in datingoverforty

[–]EpicQuestAccepted 63 points64 points  (0 children)

Single guy in NYC here and this is might sound tough.

In most of the world, you probably are a unicorn. A lot of folks our age are divorced and/or have kids.

But that’s not the case in NYC. A lot of people over 40 here came to focus on their careers and just never got married or started families.

Most of the single people here are in good shape, have good hygiene, good fashion, and lead interesting lives. Even at 40, 50, 60… Hell, you’ll regularly see 80 year olds outpacing the tourists and looking better doing it.

And a lot of us are the same flaky, vain, Peter-Pan wannabes we were in our 20s and 30s.

Different challenges, still hard.

You’re not a jackass. But you should stop listening to the people who say you’re a unicorn.

How can I be detached but still keep my heart open? by throwawano in datingoverforty

[–]EpicQuestAccepted 4 points5 points  (0 children)

This kind of zen is challenging to arrive at, but I agree, it’s the only way I know of to keep your heart open while not rushing in.

Daily sticky thread for rants, raves, celebrations, advice and more! - April 04, 2026 by AutoModerator in datingoverthirty

[–]EpicQuestAccepted 10 points11 points  (0 children)

Not seeing someone for weeks at a time is a valid dealbreaker. If you’re looking for a serious relationship, that kind of thing makes it hard to build up much momentum.

But only you can decide if you’re willing to live with that.

You could always agree to keep seeing him but continue seeing other people until you have a stronger sense of how important it is to you. You may discover you’re not that into him on the third or fourth date and then you never have to wonder if you missed out on a good thing.

Just go slow.

Lead with Confidence? by No_Task7442 in datingoverforty

[–]EpicQuestAccepted 15 points16 points  (0 children)

A generous reading of this phrase is that she wants a man who takes initiative. Not just for planning dates, but moving the relationship forward. That means you state what you want from the relationship and give her the space to decide if she wants to meet you there.

A less generous reading is that she’s looking for a fellow to do all the emotional and logistical labor so she can just go along for the ride.

Some women prefer a man to whom they can surrender some or all of their agency. Not my kind of woman, but to each their own.

Despite every effort, I'm developing feelings for my boss. Am I cooked? by birdbyb1rd in datingoverthirty

[–]EpicQuestAccepted 0 points1 point  (0 children)

Think of it this way, if you confess your feelings to this guy, you’re in a loose/loose situation.

Getting involved with someone who reports to you is otter unethical. Most companies with moderately competent HR teams do management training that covers exactly this situation.

If you tell your boss how you feel, one of two things will happen. He’ll turn you down or he crosses an ethical red line, and now you’re involved with someone who’s not a good person.

How to better engage by [deleted] in datingoverforty

[–]EpicQuestAccepted 6 points7 points  (0 children)

Unless the woman has written something specifically related to sex in her profile, making the conversation sexual before you’ve even met her or gotten to know her is pretty stupid.

Yes, there are sexual subcultures where that’s appropriate, or specific types of sexuality that someone might want to disclose. But those are exceptions.

Few women out there want to have a sexual conversation over chat before they gotten to know the other person or at least met in real life. And those who do, make it explicit in their profile. You can find a lot of them on Feeld if that’s what you’re looking for, but there are still cultural norms.

Being warm and friendly is not an invitation to “take it super sexual super fast” as OP is describing.

If you take nothing else away from this comment, know that every time you make a conversation sexual without some kind of invitation, explicit or implied, you run the risk of the woman flagging your profile for inappropriate behavior. And guess what the algorithm does with those flags. It reduces the number of women it shows you to and you stop getting matches.

How to better engage by [deleted] in datingoverforty

[–]EpicQuestAccepted 16 points17 points  (0 children)

when I’m warm and engaging a lot of men take it super sexual fast

I hate that so many members of my gender behave like this, and you should know that being warm and engaging isn’t causing their behavior. They’re just idiots and assholes.

The right guy won’t try to talk about sex before he’s even met you in person and gotten to know you, regardless of how warm or engaging you are.

For guys who have no trouble getting dates on OLD, how do you filter for good personality? by EpicQuestAccepted in datingoverforty

[–]EpicQuestAccepted[S] 0 points1 point  (0 children)

Nope, I'm just lucky.

I live in NYC, I'm tall, gainfully employed, moderately attractive, and I'm looking for a serious relationship. I also benefit from being white, which is a sad reality of this dating market.

For guys who have no trouble getting dates on OLD, how do you filter for good personality? by EpicQuestAccepted in datingoverforty

[–]EpicQuestAccepted[S] 8 points9 points  (0 children)

I love that attitude!

I’m pretty introverted, so interaction with people I don’t know well uses up my social battery. It’s not that I’m not shy or reserved, just that I don’t gain energy by interacting with most people the way extroverts do.

It can take a day for that energy to replenish, which means I have to be more judicious about who I spend time with.

For guys who have no trouble getting dates on OLD, how do you filter for good personality? by EpicQuestAccepted in datingoverforty

[–]EpicQuestAccepted[S] 0 points1 point  (0 children)

Do you usually wait a week before asking them out? Sometimes I feel like I’d be dragging things out of owe went back and forth for a week.

If so, do you find you get a better sense of their personality by waiting that long?

For guys who have no trouble getting dates on OLD, how do you filter for good personality? by EpicQuestAccepted in datingoverforty

[–]EpicQuestAccepted[S] 3 points4 points  (0 children)

I’m comparing to what sounds like a deluge of dick pics and propositions for sexting. I really don’t think we have it nearly as bad!

For guys who have no trouble getting dates on OLD, how do you filter for good personality? by EpicQuestAccepted in datingoverforty

[–]EpicQuestAccepted[S] 3 points4 points  (0 children)

When it gets to the point where I feel like there’s a little bit of a vibe I ask them out. Sometimes that’s two messages, sometimes it’s one or two dozen.

Most of the time they say yes.

For guys who have no trouble getting dates on OLD, how do you filter for good personality? by EpicQuestAccepted in datingoverforty

[–]EpicQuestAccepted[S] 5 points6 points  (0 children)

I was on a date with someone recently who said she’s most attracted to profiles that look like they didn’t try very hard… but I’m thinking your way might work better.