Dating 30+ - /r9k/ (#82220894) [Archived: 242 hours ago]

Anonymous
8/18/2025, 5:38:47 AM No.82220894
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md5: cd295f83869f3c421c346fa353c62e0d🔍
>30+ virgin
>Got my first actual date when I was 29
>Try Hinge +, got another date off that with some ugly black girl
>We both weren't feeling it
>fast forward 3 years
>meaningless, stilted conversations that end after 2 days with hinge girls
>almost got a hooker after a wedding i went to, instead just wasted a lot of money on a stripper and jacked off
>Go out with friends (they're normal)
>Friend invites female co worker who invites female friend
>Friend is interested in co worker
>other friends are all with their girlfriends
>see that these 2 girls aren't talking to anyone
>they are both super cute
>fuck it I say
>Turn around start talking to them
>Internally accept that I have zero chance but can at least set the stage for my friend
>I've been told by many people that I'm really funny and enjoyable to talk to
>Just vibe
>2 hours later
>making this other girl smile and laugh
>decide to take a shot
>ask for her number
>she replies "I was waiting for you to ask that"
>flash forward 3 hours (12 am)
>Four of us still talking, other friends left
>Go to a second bar
>2 am
>the girls leave together
>me and friend get food and relay details
>feeling hopeful
>next morning, decide to text her and ask her out for dinner
>no reply
>figures
>5 hours later I am taking a late shower
>she replies
>Says she would love to go out with me
>Shes in medical, doing a residency so her hours are complete trash
>we settle on a thursday date a week and a half later
>Some texting everyday, she always replies super late or early due to her shifts
>super cutesy in her texts, smiley faces, gifs, etch
>Date comes up
>Feel a mixture of apathy and nervousness
>Got a reservation for a nice Italian spot by her so she can walk over after work
>We meet up
>Dinner is nonstop chatter
>9pm she looks at her phone and says she really needs to leave since she has a 4am shift
>I walk her back to her bike (we're in the city so I ubered to avoid issues with parking)
cont.
Replies: >>82221008 >>82221383
Anonymous
8/18/2025, 5:43:37 AM No.82220938
Finally a greentext story. It's been so long.
Replies: >>82220954
Anonymous
8/18/2025, 5:44:50 AM No.82220950
Dating at 30+ is just going to the bar and meeting people. Only problem is you have to like being around alcoholics.
Anonymous
8/18/2025, 5:45:10 AM No.82220954
>>82220938
greeen
Anonymous
8/18/2025, 5:52:34 AM No.82221008
>>82220894 (OP)
>We talk about a trip she's making.
>She's gonna go some third world country and do humanitarian work for a full month in septemeber
>walk is shorter than expected
>she starts walking into the garage
>off guard I ask if I can see her again
>She turns around and smiles sweetly
>of course!
>Feeling good the next few days
>Texting continues
>Friends tell me I should have made a move by now since most likely she's down to fuck already
>Even assure me that women don't view attractivness the same as men do
>I agree since I realize there are a bunch of losers and ugly guys with hot girlfriends
>Same night, during our texting I ask her out again
>Tell her to let me know when she's free since I'd love to take her out again
>wait
>Late night reply as always
>"I would love to go out with you ..."
>"but my schedule is super bad right now and I don't want to lead you on with being wishy washy about my free time"
>I feel nothing beyond mild disappointment
>Reply back with a "no worries, if your schedule does open up just let me know"
>she replies with a thank you
>Its been a week
>no more texting
>I had zero faith that she was being legit and was just letting me down gently
>Plus she's gonna be gone for a full month soon

I don't know how I should feel. Good i guess, since i made it further than I thought? Bad becasue I fumbled a hot girl who was interested in talking to me? Despaired because I realize I exude ZERO sexual energy? I had her laughing, but I couldn't segue that into getting in her bed. I'm just some dude she had a nice talk with. I don't even know how to be flirty in this day and age without coming off as a creep. Maybe I should just be full cheesy and say some cringe as shit like you look beautiful or a man should always pay the bill for a gorgeous woman. It's better to be cheesy than creepy right? I don't know.

I just don't know where to go from here. Everytime i get a notification i hope its her texting saying shes free.
Replies: >>82221043 >>82221287
Anonymous
8/18/2025, 5:56:47 AM No.82221043
>>82221008
The only net positive I gained from this is the knowledge that I can talk a girl into a date if I can get her attention.

My friend put it best, that going on a date and just talking to girls is fun. And he was right.

Just talking to her made me try harder in my life.I was working harder, playing less games and keeping my apartment cleaner. Even after a week I feel a little better than I did before. I'm getting older, and maybe I'm hitting my stride.

The money on the date doesn't worry me, I spent 3 times as much on stupid ass hobbies I've had.

Part of me can't help but hope that after her trip she'll actually text me. But I know it's all bullshit.
Replies: >>82221217 >>82221819
Anonymous
8/18/2025, 6:23:47 AM No.82221217
>>82221043
Hold onto that hope anon. I am manifesting a happy ending for you. Hang in there
Anonymous
8/18/2025, 6:29:35 AM No.82221244
>>she replies "I was waiting for you to ask that"
Not sure I'm overthinking but this makes me think she's experienced and already knew you were less experienced than her.
>>Friends tell me I should have made a move by now since most likely she's down to fuck already
This is such a complicated dance man. What if I don't want to have sex right away, do they lose interest if you aren't sexually pushy? If so, I'm fucked.
Anonymous
8/18/2025, 6:36:07 AM No.82221287
>>82221008
I'm a 30+ guy just getting into talking to women after a decade of utter stagnation
I can get sexual and flirt though text and get some really good connection going but it's only been online from distance so far so it's pretty removed from being able to take it to real life connection. Everything so far has ended in the same disconnect before a meetup was planned

I need practice dating irl and you should use online connections to practice the flirtation/sexual side of it
Then we combine those and hopefully actually get somewhere
You have it easier I think
More of a barrier to doing shit irl
Anonymous
8/18/2025, 6:42:34 AM No.82221314
if you actually wanted to fuck her you would make a proper move on her, not just sit around waiting for something to happen, she must have been boring and plain
Replies: >>82221329
Anonymous
8/18/2025, 6:44:29 AM No.82221329
>>82221314
You do not understand the mind of a 30+yo virgin
Sexual energy is the last thing but natural
It's basically foreign, like you have to reverse engineer into it and it will still mostly fail. Normalfags wouldn't understand
Replies: >>82221536
Anonymous
8/18/2025, 6:55:02 AM No.82221383
>>82220894 (OP)
You're doing fine, you can actually keep them engaged, I'm sure you'll eventually find a way to flirt with them if you practice your skills by going out more regularly. I personally just started uni and I'm a failure at keeping interesting convos going, so it could be worse for you, play the hand you were dealt and everything will turn out just fine.
Replies: >>82221453
Anonymous
8/18/2025, 7:10:30 AM No.82221453
>>82221383
I mean talking comes easy to me. I do find it fairly easy to get people to like me since I hit this sweet spot of friendly and catty that makes people laugh and be at ease. I shit talk well and can take shit talking also which means I'm pretty good at getting people to open up.

But this was like the first time in a really long time that I talked to a girl who wasn't one of my friends girl outside of a work function.
Anonymous
8/18/2025, 7:13:38 AM No.82221478
So Im 30 and my friends just made fun of me for missing "obvious" signals from a woman at work.

>She called our work call center to get my number
>We started talking about nonwork family shit
>I went to a work event for her and she hugged me multiple times.

I only see her at work, but at this point I want to ask her out. If you had to guess, what's your guess at what the chance she actually does like me if she called my job and told me she switched employers?
Replies: >>82221527 >>82221633
Anonymous
8/18/2025, 7:20:54 AM No.82221527
>>82221478
>She called our work call center to get my number
>I went to a work event for her and she hugged me multiple times.
>she called my job and told me she switched employers
Alright.
>what's your guess at what the chance she actually does like me
Extremely high, I'd advise you act sooner rather than latter.
Replies: >>82221727
Anonymous
8/18/2025, 7:22:21 AM No.82221536
>>82221329
idk im 28 next month and horny as fuck on my own but women are just plain and cunty to me
Anonymous
8/18/2025, 7:38:33 AM No.82221633
>>82221478
If she no longer works with you and you like her even I know there is zero harm in asking her out. You really got to get into the mindset that its better to fail than to not try at all.

Your friends will make fun of you more for not asking her out than they would if you asked her out and got shutdown.

You don't even need a preamble really. Just a " I was wondering if you wanted to go out sometime"

At this point shes probably going to say yes. If she says no, that's cool just carry on with you life and forget it.

YOU need to pick the spot, you can ask her for food themes etc but its really important that you take the initiative

>Ask her at some point/make the leap what she's looking for romantically or something along that line. Basically get it across that you are interested in her in romantic sense. You're gonna have to make some judgement calls in case she's just a freak whos down to clown and isn't looking for a relationship and adjust accordingly
>Try to end the night on your terms. If the vibes are good maybe go in for a kiss or more. at the very least make a memorable exit even if its just you telling her you want to see again. Girls are expected now to give it up on the first or second date if it goes well, especially at that age. If she's respectable, maybe the third.
>Remember that girls don't really care about dick size that much beyond bragging rights or potentially a way to hurt you. Unless you have a micro penis, she is going to be able to make it work. if you want to make her happy, you're gonna have to work on your foreplay/eating out skill.
>If you are white, be extremely careful about making any edgy jokes politically or racially. You do not have the same initial credit a minority does to say some insensitive things.

So yeah, i say ask her out and just take a shot at this point. Unless you go crazy the worst she can do is say no.
Replies: >>82221727 >>82221739 >>82221739
Anonymous
8/18/2025, 7:56:01 AM No.82221727
>>82221527
I have to ask a woman out now, let's see how that goes.

>>82221633
I text her and essentially invited myself to her new jobs ribbon cutting event, thats when that hugging happened. At this point Ive decided I need to just ask her out outright to avoid any confusion or delay.

Honestly, Im crossing my fingers and balls that she is into me rather than misinterpreted signs.
Replies: >>82221766
Anonymous
8/18/2025, 7:58:27 AM No.82221739
>>82221633
>>82221633
>penis size
I have a pretty big penis, Im really not concerned there. If Im concerned about anything its just "30 year old man is attracted to 24 year old woman, also doesn't know how to hit on women"
Replies: >>82221890
Anonymous
8/18/2025, 8:04:10 AM No.82221766
>>82221727
Good luck man, given how she's frankly put herself into awkward situations into keeping in contact with you I think your odds are great. And if you get a thing going keep that effort she put forward in mind, generally people act like how they want others to act (within context). So they will likely appreciate you acting proactive.
Replies: >>82221800
Anonymous
8/18/2025, 8:09:38 AM No.82221800
>>82221766
We're going to see how it goes. I like her, Im like 50/50 that she likes me, and it feels like I need to just ask her out and figure it out now.
Anonymous
8/18/2025, 8:12:51 AM No.82221819
>>82221043
>My friend put it best, that going on a date and just talking to girls is fun. And he was right.
Puke
Anonymous
8/18/2025, 8:25:03 AM No.82221890
>>82221739
>30 year old man is attracted to 24 year old woman
Lol real
I got treated like a pedophile for talking to a 24yo while 32
Shit's kooky
Replies: >>82221956
Anonymous
8/18/2025, 8:39:15 AM No.82221956
>>82221890
I think realistically its been in my own head. I know when I talked about that concern with friends they were all like "a y year gap for adults is nothing to write home about,", but Im still subconsciously giving myself reasons to avoid it.

I know I like her, I know I want to be with her, and I think she wants to be with me, but my thoughts are filtered through the vacuum of 8 beers and also a Scandinavian Festival today. So who knows.

All I know is friday when she hugged me while wearing a dress I spent that night wondering if she knew I could feel her hips and tits against me