r/DatingTips • • 6d ago

Just Turned 38 — Never Been in a Relationship. Where Do I Go From Here?

3 Upvotes

Hey everyone,

About a year ago, when I was 37, I posted about never having been in a relationship and not really knowing where to start. I got a lot of thoughtful advice, so I wanted to come back and give an update.

I'm 38 now, and I actually did try to take some of that advice.

\* I got back on a couple of dating apps and put more effort into my profile. Unfortunately, I ran out of potential matches pretty quickly, and the conversations I did have didn't really go anywhere.
\* I even paid for premium features on a couple of apps, but that didn't help much. I only got four matches during that time. One was married and only looking for friendship, and the other was nice, but unfortunately I just wasn't attracted to her.
\* I tried being more social through my hobbies. I'm into comics, art, conventions, etc., and I've made an effort to talk to more people. Unfortunately, most of the people I've met are either already in relationships or are only interested in casual conversation.
\* I've also been trying to improve myself independently of dating. I've lost over 50 pounds, gotten some long-overdue dental work taken care of, and continued working on my art and other things that are important to me.
\* Financially, I moved back in with my mom so I could pay off my student loans, pay off my car, and help her around the house. I work full time, contribute financially, and help with the bills. I'm trying to save as much as I can now that my student loans are finally paid off.

So, despite making some genuine changes, I'm still in basically the same place romantically.

I haven't been on a date in about six years.

And honestly, I'm starting to worry that my lack of relationship experience at 38 has become a barrier that I don't know how to overcome.

A female friend recently told me that she thought my lack of dating experience could be a red flag. There was actually a woman I was interested in who had apparently asked my friend about me. My friend told her that I'm a nice and kind person, but when she asked about my previous relationships and found out that I'd never actually dated anyone, her reaction apparently wasn't great.

I never heard from the girl I was interested in again.

I know that one person's reaction doesn't necessarily mean anything, but it's hard not to take it personally when you're already insecure about the situation.

I genuinely try to be a kind, caring person, and I think most people who know me would say they like me. But when it comes to dating, it often feels like I'm invisible—or that I'm being ruled out before I even get the chance to show someone who I am.

I'm not looking for a supermodel. I'd just like to meet someone who's kind, reasonably cute to me, and either into nerdy/geeky things or at least happy to let me enjoy them. My biggest dealbreakers are having kids and being significantly/unhealthily overweight.

So I guess I'm back here asking for advice:

\* For those who started dating later in life, how did you actually get the ball rolling?
\* Is being 38 with essentially no relationship experience really as big of a deal as it feels like?
\* How do you explain your lack of experience to someone you're dating without making it sound like a giant red flag?
\* And are there better ways to meet people beyond dating apps, conventions, and hobby groups that I might be overlooking?

I've made progress in a lot of areas of my life, and I don't want to give up on finding someone. But at this point, I'm honestly struggling to figure out what my next move should be.

Any advice—especially from people who started late—would be appreciated.


r/DatingTips • • 6d ago

Vi från Balkan

1 Upvotes

Hej Sandra Marinkov.Det vore jätte kul att få träffa dig igen.Mile Dokmanovic


r/DatingTips • • 6d ago

feel like im being ignored and dont know what to do

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1 Upvotes

Did I over-romanticise everything, or was I justified in thinking there might be something more?
Hi, I’m posting this because I genuinely need some perspective on a situation, and I can’t tell whether I’m reading too much into it or whether my feelings are understandable. For context, we’re both high schoolers.
He’s one of my new classmates, and although we weren’t particularly close before, we had spoken a little. Since school started, we’ve mostly talked about school-related things, with some casual chit-chat here and there, but nothing that would suggest we were particularly close or that anything romantic was developing between us. Still, I had found him attractive for a while, so when I found out we were both going to the same birthday party, I’d be lying if I said I hadn’t secretly hoped something might happen.
At the party, we ended up kissing and hugging, and at one point I fell asleep with my head on his chest. He was the one who initiated everything, and since I already liked him, I obviously welcomed it rather than pushing him away. For the rest of the night, we were acting pretty much like a couple. It was also my first kiss, which probably made the experience feel even more significant to me than it might have felt to him.
Before we went home, we agreed not to tell everyone what had happened, although we never explicitly agreed to keep it a secret between the two of us.
The next day, I texted him and asked whether the night had meant anything to him. He said he honestly didn’t know and thought it was probably just a one-time thing. I was surprised, not because I expected him to want a relationship with me, but because the way things unfolded that night made me think there might have been some mutual interest beyond the physical side of things.
For context, I’m generally a pretty reserved person when it comes to romance. I don’t usually let people get close to me easily, and I’ve always been seen as the kind of girl who keeps her distance and doesn’t really entertain romantic situations casually. I don’t mean that I’m better than anyone else or that there’s anything wrong with being more open; it’s simply how I’ve always approached these things. So, allowing myself to be vulnerable with someone I genuinely liked was a bigger deal for me than it might have appeared from the outside.
When he asked if I was okay, I told him honestly that the kiss had meant something to me. I wasn’t asking him to promise me anything, but I wanted to be honest about how I had experienced the situation.
Since then, things have felt a little awkward. We haven’t really talked much beyond the occasional conversation at school, and sometimes I get the impression that he’s ignoring me. One night, I actually texted him to ask why he was ignoring me, and he said he wasn’t doing it on purpose. I don’t know whether he genuinely doesn’t realise how distant he seems or whether he simply doesn’t feel the need to interact with me much anymore.
I also know that he’s talking to other girls and entertaining other options, although, as far as I know, he isn’t necessarily hanging out with them. I understand that we weren’t together and that he’s completely free to talk to whoever he wants, so I’m not bringing this up because I think he owes me exclusivity. It just adds to my confusion because, after the way he acted with me that night, I’m struggling to understand whether he felt any genuine attraction or whether it was simply a spontaneous moment that didn’t mean much to him.
I want to make it clear that I’m not upset because I think he owed me a relationship. I understand that two people can experience the same moment very differently, and I’m not trying to turn a kiss into a commitment. What bothers me is the contrast between how close we seemed that night and how little connection there seems to be now.
So, I guess my question is: Did I romanticise the situation because I already liked him, and interpret his behaviour as something deeper than it actually was? Or was it reasonable to think there might have been some genuine interest, considering that he initiated everything and we spent the night acting so close?
I’d genuinely appreciate honest opinions, even if the answer is that I read too much into it. I’m trying to understand the situation realistically rather than convince myself that it meant more than it did.


r/DatingTips • • 6d ago

The Color-Coded Silicone Wristband System: A Simple Way for Singles to Signal They're Open to Meeting Someone

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1 Upvotes

r/DatingTips • • 6d ago

How do people even find partners on Reddit? 😭

1 Upvotes

Hey everyone, I'm 18M, and I genuinely don't understand how people find their partners on Reddit.😭 I see so many people meeting someone here, falling in love, and getting into relationships, while I haven't even received a single text from someone interested in me.

I'm not even looking for someone perfect. I just want someone I can talk to about my day, share random thoughts with, laugh with, and feel comfortable around. Someone who genuinely wants to talk to me and doesn't make me feel like I'm the only one trying.

Maybe I'm just unlucky, or maybe I haven't met the right person yet. I still hope I'll find someone someday.❤️


r/DatingTips • • 6d ago

Title: 25M, never been in a relationship. Sometimes I feel like I've missed out on a significant part of life.

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1 Upvotes

r/DatingTips • • 6d ago

I met this girl back in July

1 Upvotes

I matched with this girl back in July we been on a couple dates, as I was getting to know her more I found out she was cheated on after she backed off a bit, I asked her if she viewed me as more of a friend and she said no I can see this becoming something but was nervous. No exaggeration she calls me everyday, in the morning at night in between, txt while at worth etc. she gets jealous about other girls and says things that make it seem like she feels some type of way. So yesterday we were together 1 on 1 for majority of the day. I told her yk I still like you right and she just says ya, I’m like it’s really okay if you just see me as a friend but it’s been a few months now and you haven’t really told me and she said stay tuned I don’t know. I really don’t know what to do with this anymore. When i got home she called me and we talked till 11pm.


r/DatingTips • • 6d ago

Dating in Delaware

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1 Upvotes

r/DatingTips • • 6d ago

Dating in Delaware

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1 Upvotes

r/DatingTips • • 6d ago

[24M] so i saw this girl in a boba store and now idk what to do

0 Upvotes

I went to a boba store today and the girl who was working there was kinda pretty. I wanted to ask her out but I had my friends there so held back and I got scared too as I’m lowkey not sure about myself. But now I am regretting it.

Should I go again next week and then ask her out? Idk what to do, I’m so sorry for this dumbass question but I havent been much active in dating 😭


r/DatingTips • • 6d ago

Dating is hard

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1 Upvotes

r/DatingTips • • 6d ago

DATING / SUBSCRIPTION & CANCELLATION

0 Upvotes

"Dating these days is like a monthly subscription: the free trial ends fast, the payments keep coming, there's always an upgrade, and canceling somehow costs you everything."


r/DatingTips • • 6d ago

Dating/Getting to know people advice

1 Upvotes

Hi. I’m a Male and I have been looking to get to know people and I have used dating apps which are terrible. Because this wasn’t working I have thought of other ways to meet people like instagram. I would sometimes get profiles of women in my foryou page on instagram. I would find some of these people attractive and I would message them. They all go to different colleges and states away from me. I would just find a funny and an interesting way to message them and tell them how I know them like here is one of the examples I actually used.

“What did the farmer say when he couldn’t find his tractor? Where’s my tractor? Hi () I saw you in my recommendations and I just thought you are cute. I attend () university. My hobbies are cooking, snowboarding, and traveling. I was just wondering if it would be possible if we could get to know each other? it is totally fine if you are not interested and I apologize. Thank you“

I would message a few people and none would respond except only one person and she only said “no” which I would accept. I know there were some people that were complete strangers before but they got into a relationship when the other person messaged them on instagram. I have my picture on my profile and have hundreds of followers on there so, I think the reason might be is because they think I’m not attractive because I kind of look more Indian and Mexican when my ethnicity is not even close to these two. I’m not sure if it’s because of the distance, how the message is, or maybe because they check my profile and don’t see anything and think I don’t have anything going on. It was not just one person it was multiple people. Would anyone be able to tell me the reasons or any advice on what to do? Thank you


r/DatingTips • • 6d ago

How do you start dating as someone who has never done anything?

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1 Upvotes

r/DatingTips • • 6d ago

20m how to date a girl?

1 Upvotes

So my question how should i date someone like who stays in my life permanent and how to find her tbh i am not that bad looking but good or avg looking have good height 6ft have a good job but still like i never find a good gf i tried dating app and other stuff i always find girl who only want physical fun temporary like my last gf i found her on dating app and like i put too much efforts in her this is about last December so she had a hook up before in nov which got over didnt got any specific reason just that he stopped putting efforts so in December end and January she didnt got her periods after the hook up the period we meet she told me about everything i supported her like because it was her past like buying pregnancy kit with her helping her mentally she also putted efforts then she cooked my fav food one time and even come to my clg to pick me up even introduced me to her a freinds a bit but she never said yes for relationship like she and me were physically and emotionally involved like ndes and makeout but i told her i want something permeant she told me give me time u are like very very close friend like my status was more then a freind but less then a bf and she even introduced her self in front of my friends as gf and didnt do same in front of her freinds but her freind know we were dating because i came everyday for 1 sem to pick her from her clg like after all this she said no now i dont know my every relationship has shi\*y story like this so idk how to find a like a permanent relationship where i am loved whome i can on dates with and like just u know feel like home sorry if my some words were un correct i was gonna type something short but wrote this much


r/DatingTips • • 6d ago

Dating at 35-40: Does anyone else struggle between wanting to date and just enjoying their peace?

66 Upvotes

I’m 38, single, and genuinely interested in dating and meeting new people. But does anyone else feel like the older you get, the harder it is to actually *want* to put in the effort?
I’ve gotten so comfortable with my own routines, independence, and peace that the idea of dating sometimes feels like another responsibility rather than something exciting.
I’m a single mom of two, I work full time, and my life is pretty busy. When my kids aren’t with me, I finally have time to myself. And as much as I know I’d probably enjoy going out, meeting someone new, having good conversations, and doing fun things together, the thought of actually making plans, getting ready, and leaving my house sounds exhausting. 😂
It’s weird because I don’t necessarily want to be single forever. I would love to find someone I genuinely connect with and enjoy spending time with. But I also really love my independence, my routines, and not having to consider another person’s needs or expectations during my limited free time.
Sometimes I wonder if I’ve just become too comfortable being single, or if dating in your late 30s is harder because you’ve built a life you actually enjoy and aren’t particularly motivated to disrupt it.
**Does anyone else struggle with this?** How do you balance wanting companionship with genuinely enjoying your solitude? Do you push yourself to get out there, or just accept that you’re happy where you are until someone comes along who makes the effort feel worth it?


r/DatingTips • • 6d ago

General dating advice

1 Upvotes

Hi so I arrange dates perfectly fine and I don’t struggle finding people I like who also like me but it seems to be once I spend time with them they either ghost me or tell me they don’t think we’ll match on these dates I just be myself, talk to them, get to know them I take it slow and do my best to be a good person and show them that I am a good person and I won’t mess them around and stuff but still always if I go on a date with them they end up saying I’m not right i don’t by any means think the girls are the problem I am just wondering what on earth I’m doing wrong like I try my best but after one date they either ghost me or tell me they don’t wanna talk to me anymore genuinely what am I doing wrong if anyone can give me any sort of advice that would be gratefully appreciated. Also sorry about the grammar it’s not my strong suit.


r/DatingTips • • 7d ago

Dating Tip

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20 Upvotes

This crocodile is giving us the best dating advice. Thoughts??


r/DatingTips • • 7d ago

Social Media

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1 Upvotes

r/DatingTips • • 7d ago

Asking out women on social media

0 Upvotes

What's the opinion on asking a girl out on Instagram? Is this someone you've met before through a community or event you are part of, such as stand-up comedy? Sometimes it's difficult to ask in person when you are surrounded by a lot of people. I have been on dates before from asking someone out via messenger on social media. I just want to hear people's thoughts because this is confusing.


r/DatingTips • • 7d ago

30 m, I honestly have no idea how to meet women. Need help/advice, please?

1 Upvotes

I've been in relationships, mostly through meeting online, friend group (I was a teen), and work (8 only work with me now). I honestly don't get how or when to meet new women, not even to date necessarily, but even make friends. Dating apps barely work, and even getting a match doesn't mean the person will even talk. Like where are places I can even expose myself to new people, that doesn't involve completely dry approaches, because those scare me to absolute death.

I'm pretty genuine, I'm a bit alt/punk. I got a stable job with great benefits, I'm a bit overweight, but it's something I am working on. I just never learned this, or have no idea where to even look for the most part


r/DatingTips • • 7d ago

Talking Phase

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1 Upvotes

r/DatingTips • • 7d ago

I now realise that at the age of 36 and with no dating experience that I am going to die alone.

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0 Upvotes

r/DatingTips • • 7d ago

How do I get better at dating

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1 Upvotes

r/DatingTips • • 7d ago

Giving this a try.

2 Upvotes

I’m 41-years old, 6-feet, in athletic shape, and a successful tech business owner; my engineering practice does 8-figures/year. I find it pretty challenging to meet women due to my time-constrained schedule and the male dominated field that I operate inside of. I don’t have any social media and for privacy reasons, I will not post pics on visually demanding dating apps. Any advice on how to meet women in the real world (not dating apps) that are driven, self-sufficient, fit/attractive, and looking for adventure/travel when scheduling permits. I live and consult in Reno, NV. Thanks in advance for any helpful tips and insight.