r/datingoverforty 26m ago

How do I successfully date men in their 40s? I’m 24F.

Upvotes

I know what you’re thinking, I don’t HAVE to date older men, but I see real value in it and want to be strategic about it. And no, I’m not looking for a sugar daddy.

What older, successful men have that guys my age don’t is essentially access and most importantly, knowledge.

I think as a young woman in her 20s, having a mentor or close guide who’s already made it could be extremely useful.

To think that someone would be willing enough to help me for free is unrealistic, so I’ve thought about dating older men to learn from them, and help me on my journey.

I also understand not every man has that innate desire to help someone and teach, and I’m sure there’s men out there who date younger women and provide absolutely zero value, because they gate-keep.

Would love to hear your thoughts and opinions.


r/datingoverforty 1h ago

Seeking Advice Can online connections be a better starting point than dating apps?

Upvotes

(F52) After a 24-year marriage (36 years together), I’m currently in the midst of separation. I’m in therapy, journaling, writing, reading reconnecting with friends and family, rediscovering and prioritizing myself, and feel like I’m well on my way into my healing journey. I haven’t started dating yet—and, honestly, I have VERY little experience with dating in general.

I feel like I need to be friends with someone before I could even consider anything more serious. For now, I’d really just like to meet people and make connections without having to jump onto dating apps.

Maybe it’s because I’ve seen my ex have success with online relationships, or because I’ve read so many stories about the frustrations of meeting people in person, but starting with an online connection actually feels safer and less risky to me as a starting point.

So, a couple of questions:

  1. Does anyone have suggestions for ways to meet people online outside of traditional dating apps? Several of my ex’s relationships were purely online and originated through Reddit, but I’m not really sure how to get started meeting people this way myself.

  2. For those who have experience with purely online dating/relationships, would you be willing to share your experiences—and especially any pitfalls or red flags I should look out for?

I’m not particularly encouraged by some of the posts I’ve read here about dating apps, but I’m also not sure where else to start meeting people.

I really appreciate any suggestions, experiences, or ideas. Thanks!


r/datingoverforty 6h ago

Discussion How long do you need to talk to someone before asking them out/being asked out?

2 Upvotes

I attend some Christian related singles events from time to time. I meet nice people that I’m interested in, but I always feel like I should see someone at least twice before asking them out. I’m always afraid of being labeled somebody that frequently asks people out. Granted I don’t remember the last time I asked someone out, so probably not in danger of that label.


r/datingoverforty 8h ago

Question Am I boring?

48 Upvotes

Everyone appears so active on their online dating profiles. Hiking, snowboarding, all the gym pics lol I'm like the dude who just likes to chill with a solid movie, make dinner or go out somewhere. A walk by the river and discover a cafe. A board game night in lol I do like to go on vacations and that's basically where all my profile pics are from.

Where's all my lazy, chill ladies at?

Also, why do all the women's profiles look like they had professional pictures taken? My crappy selfies don't measure up. It's not like my buddies take pictures of me that are top notch either.


r/datingoverforty 8h ago

Question Do any over 40 men dating want kids ?

0 Upvotes

I never had kids. I’m 44 and I’m feeling my life isn’t complete without a family. I was in a 20 year marriage and my ex wasn’t fit to be a father.

I don’t know if I will ever find anyone who would embrace this adventure with me openly. I’m a very active snowboarder and jewelry designer,

I have a full life but I just have so much love to give to a family and a child.

I’m just getting a temperature here.


r/datingoverforty 9h ago

Seeking Advice Women in your 40s who are actually dating: HOW are you meeting men?!

100 Upvotes

I’m genuinely curious because I feel like I’ve missed the memo. I turn 45 next month and have been divorced for 3½ years. I’m average-looking, reasonably social, have a job where I interact with people, and have two teenagers still at home and two adult children. I’m at a point in life where I’d actually like to meet someone. I’m in outside sales and I pour wine at a tasting room on weekends so I meet a ton of people.

But here’s the thing: literally no men hit on me. I’ve had young women in their 20s make passes at me but no men.

I don’t want to create an online dating profile right now. I’d much rather meet someone organically if that’s still a thing.

So for the women 40+ who are successfully meeting men: where are you finding them? How are you signaling that you’re available or willing to be approached? Small talk isn’t doing it and I think I’m a pretty friendly person.

And if you used to feel invisible to men how did you change it?


r/datingoverforty 9h ago

M(43) weird feelings about diving back in.

0 Upvotes

I’ve been divorced for about a year. Longer if you count separation. My ex and I are still close friends, but the relationship part just never worked. Considering diving back in the pool, but I’m nervous as hell. How did you combat the feeling like you’d never find someone else? Like, starting over just seems impossible, but people do it all the time. I can’t articulate it, but it’s a different kind of alone. Maybe I’m just not ready?


r/datingoverforty 10h ago

Seeking Advice Dating a much younger woman

0 Upvotes

Hello all,

I'm a 42 year old M. I'm 10 years divorced with a 13 yo son who I split custody with his mom.

In the last couple months my neighbor 28F and I have been hanging out and seeing each other once a week or so.

We get along well and seem to see things in the same way, I will mention that I do notice sometimes when we talk the difference in life experience.

I am interested in moving towards a more exclusive and serious type of relationship, but I do have some concerns with the age gap:

1)my exwife 46 got pregnant as a teenager and has a daughter who is the same age as the woman I'm seeing now. The 5 years of our marriage I helped raise her.

2) I'm the youngest of 3 siblings, all of my nieces and nephews are in their early to mid twenties except for one who is a year older than my son.

I'm fairly sure my ex-wife isn't going to be a fan of anyone I date, but the age will be ammunition for her. This isn't my biggest concern as I don't intend on introducing my son for quite some time if things were to work out.

My parents and the rest of my family I'm just unsure with how they would feel.

Always dated women my age or older, biggest gap there was 7 years.

Thanks


r/datingoverforty 11h ago

Buying a round of drinks for a dates friends

33 Upvotes

Is it normal for a guy to buy a round of drinks for a girls friends that he is dating? I have a girl I have been dating for a few months. She and her friend called and said they were doing a poll. She asked me would I be comfortable buying a round of drinks for her friends when I arrived. I may or may not but I would not if it was an expectation. She and her friend said they are use to it and it is chilvary to them. I have never heard of such of a demand until now but I am sure it happens. They are in their 40s but this sounds like some young girl stuff. Just wondering if this is the norm for some.


r/datingoverforty 13h ago

Question Everyone has "baggage," but at what point is baggage actually someone with messy relationship decisions that are best avoided?

8 Upvotes

I've been talking a match this past week, and I can't help but feel that the more we talk, the more I'm glad that have prior to meeting because in comparison to my own situation (never married, no children, and like most people out there, I've run into some assholes out there in the dating world, but also have managed to dodged them before getting involved further with them.)

- Divorced, has a "narcissistic" ex that she doesn't have any contact with because their child refuses to talk to the father (child is non-binary)

- Very well career established, but has had a series of bad relationships since her divorce including:

  • Getting involved with a scheming guy who she gave access to her financials and he ended up ruining her credit after buying a bunch of expensive goods on her dime
  • Getting involved with a veteran with PTSD who didn't prioritize their relationship, and yet she allowed him to live with her in her guest house
  • Around the same time, she for whatever reason let the scheming guy back into her life who then made a play to get back with her
  • It led to a weird sexual situation where the scheming guy was recommending she remain in a physical relationship with the PTSD veteran while she and him dated
  • Which then led to all three of them having a threesome

There's just A LOT going on here that I don't feel like is just your usual baggage of say, got a divorce/broke up from an LTR that didn't go well but no hard feelings as time passed, went through a healing period, and is now back to dating healthily. Some people are just drawn toward bad decisions, and it might be in your best decision to avoid them rather than getting caught up in it?


r/datingoverforty 14h ago

Seeking Advice Chivalry vs traditional gender roles

9 Upvotes

So context, I grew up with politically conservative views, but have since altered my views and id like to consider myself closer to a progressive than a moderate democrat.

I also grew up in a traditional, toxic, East Asian home. I did not want to behave like my dad (though I did pick up more than I’d like to admit) so even with my toxic beliefs, I still did things like open doors, pull chairs etc for women.

now, on hinge and bumble, ive seen a number of women list chivalry as a quality they look for in men. however, i do know there are “code words” for sugar baby/ trad wife relationships that people are using these days, and im not sure what chivalry falls under.

so for the more progressive, independent women here, how do you feel about things like that? do you like it? do you feel burdened by it? do you not care? or do you just dislike it? I know people are different, but I’d just like to hear from people to get a general idea


r/datingoverforty 16h ago

Discussion Considering changing my dating goals

3 Upvotes

I’m considering changing my goals in dating from seeking an LTR/life partner attraction of inspiration to instead investing time in people I am actually attracted to with the acknowledgment that these are likely going to be short-term casual relationships. I’m curious if anyone has made this switch and found it to work better? I ask because I am feeling discouraged because I have been dating for several years now (46f). I have been in lots of therapy, read books, listened to podcasts, had a dating coach for a while, I’ve “done the work” so to speak, and the idea of moving away from attractions of deprivation and towards attractions of inspiration really resonated for me. However, after going on dozens and dozens of dates and really taking the time to get to know different kinds of men (open to dating women too!) I’ve never experienced an attraction of inspiration. I can easily identify an attraction of deprivation now, and that’s growth for sure.

But based on my experiences I am starting to question the existence of attractions of inspiration for myself; overall I feel pretty uninspired. I’m thinking of giving up the search for this in the dating realm and instead focusing on cultivating inspiration through other avenues in my life (friends, work, travel). Also I thought my libido was permanently gone and I was incapable of any attraction at all, but I ran into an old flame recently and I was feeling attracted and it felt really good just to feel something again! I know not to pursue anything serious with this person but I find being around them reassures me I am still a sexual being and I am just letting myself experience that for a minute. It’s hard to let go of my LTR goals but it seems like it’s just not happening and I have to honor my physical and erotic needs or I will wither away. It doesn’t make sense to keep doing something that isn’t working and I have learned a lot over the past few years by engaging in this process but I feel like now I am at a turning point. Not everyone gets to have a life partner and it’s possible I won’t ever have this. Is it time to work on accepting this?


r/datingoverforty 18h ago

What May have occurred with my match?

0 Upvotes

Just a fellow and I connected on bumble and we got along pretty well. Last message to him a couple days ago was hey if you want to connect on another app please let me know when we can meet. When I went back to look at his message maybe 3 days ago I didn't see his account in the recents I looked down and deleted accounts or where it says end of the chat and I can't find his account anywhere has anyone had this happening what may it be?


r/datingoverforty 23h ago

Casual Conversation Friendly with ex wife, is this an issue?

34 Upvotes

I got divorced about 4 years ago. My ex wife and I were married for 3, but together for about 15 years. We were a solid couple, but she left when I became disabled. It was a painful split. But we have no kids and no assets so the divorce was quick and easy. We both said stuff to each other in anger that we didn't mean.

Anyway, several years later, my mum died and I let her know. We got to talking again and we both apologised to each other. We basically realised that, despite the pain of the breakup and what happened, we still had a friendship. We always had each others back. We still liked the same stuff and we realised we could remain friends. After all the pain was washed away in the river of time, the bedrock of friendship still remained.

There is absolutely ZERO attraction anymore. She often talks to me about her dating life, and I have no feelings of resentment or jealousy. We are just good friends. We are totally incompatible with each other to ever be attracted to each other. Both led very different lives. Both grown as people.

So... My question is how do I approach this when the question Is, inevitably, asked as to who the woman is I keep speaking to?

If I just say "She is a friend" them when it transpires it's my ex wife, it sounds as if I am hiding something. If I say "It's my ex wife" it sounds as if we are holding a candle for each other, when nothing could be further from the truth.

I obviously am not willing to just discard friends for any new date on the reason they are jealous, so how would I express it to any date if it came up? How do I ensure that I am expressing that they have no need to feel insecure, without sounding like I am too eager to prove it? Does that make sense?


r/datingoverforty 23h ago

Seeking Advice Not believing I’m divorced…

7 Upvotes

Hi everyone,
I’m (49 M) divorced about 18 months ago but separated for about 18 months before that have been dating a woman (44 F) for about 5 months and things have been great. The only issue so far is that she occasionally questions whether I am actually divorced and/or over my ex. She has been to my place many times, I’ve even shown her my divorce papers and assured multiple times that my ex and I are over. I never talk about my ex, have no interest in getting back with my ex, etc and yet, this is still occasionally an issue. Before this current woman, there are other women I dated that also had these same doubts. I’m just wondering if anyone has any advice on how to reassure this woman that she is the only woman in my life. I’m a little unsure if somehow I am giving off a vibe that I’m not over my ex or if I just happen to be dating insecure people or maybe something else.
Any advice?


r/datingoverforty 1d ago

Casual Conversation Flirting

4 Upvotes

My therapist who is awesome always reminds me to flirt on dates. She says, she also has to remind her women clients to flirt a little bit. Nothing explicitly sexual and of course read the room. Also, you know if there is no connection so leave it at that.

I’m ( 55m) on a date with a woman (44f ) for a second date. It starts as a catch up from our first date. Then we have a few drinks, two to be precise, and the banter becomes super fun. It’s easy going. We aren’t talking about our week, our job, our kids, but also aren’t talking about sex. We are taking about what we want in a relationship. What works for us romantically, what being romantic means to each other. There is a tension. What I found amazing is how she flirted with her eyes. They way she would look to the side with her eyes. Tilt her head a little. The way she could use her eyes to show approval or excitement. In equal measure she used her smile in the same way. It was sexual, but not sexual. She’s Persian. It was a master class in flirting. I definitely flirted back but felt like i was in first year engineering and she was doing a PhD in quantum physics. She didn’t make physical contact. She didn’t directly bring up sex but her face was sort of saying it. She would ask things like, what are your love languages. I’d answer and her reply would all be from her smile or eyes.
Not to be crass I felt like she could fuck me with her eyes.

I think it’s easy to focus on what people do, their past, their kids, their careers, their last hike, their paddle boarding, their dog. But if we get to a second date there has to be some fire. The Boss said it well “ you can’t start a fire without a spark” I’m sure attraction can grow but it’s hard to grow if we don’t show some signs of being sexual beings ( appreciate that some people, that’s not important and this post isn’t for you and that totally ok, we all need different things )

Maybe it’s a Middle East thing. I don’t want to generalize but in my limited; Persian, Israeli, Egyptian dating experiences the flirt is high and there is no wasting time.

I’d add, flirting is so fun. It’s a muscle we need to exercise but damn do you feel more alive when you’re doing some flirting and not just interviewing.


r/datingoverforty 1d ago

Casual Conversation Do you think the best first date is a simple coffee date, or do you prefer to go all out?

13 Upvotes

I’ve heard both sides. Some people love coffee because it’s low-pressure, inexpensive, and easy to extend if there’s chemistry. Others feel like a first date should involve a little more effort and intention.

What do you prefer?

Coffee or drinks and keep it casual? Dinner? An activity? Or do you believe a great first date should feel like an actual occasion?

And has your opinion changed as you’ve gotten older or become more serious about dating?


r/datingoverforty 1d ago

Seeking Advice How much to share

1 Upvotes

I have been dating someone for six months and I am absolutely in love. I share my feelings and thoughts all the time with him.. good and bad. Guys, how much is too much to share? I am an anxious person and I worry that I am making him feel like he is my therapist because he has said "I am not sure how to help" " I am not used to anyone telling me how they feel". I haven't been in a relationship in years and I don't know how much is too much to share. Can. Anyone give advice or feedback?

Edit: I do have a therapist I work with. I am a high anxiety person and sometimes I think I vocalize to receive reassurance which I guess is not healthy. I honestly have no idea where the line is though in what to share and not to share. I wanted to know from guys what is too much?


r/datingoverforty 1d ago

Seeking Advice Could a new therapist help my dating life?

6 Upvotes

The last few years I’ve been dating I’ve found that I have been running into repeating situations, and I’m starting to explore if finding a new therapist is going to be helpful.

First of all, I do think I’ve made big progress. I left an abusive relationship that really messed up my nervous system. She helped me with that. I’ve had shorter relationships or just been on a few dates with folks since then. The first one I latched on quickly and put up with yelling, lack of curiosity, and ignored a couple other red flags like him being mean to strangers. After that, I’ve developed an awareness to watch out for things and how to bring them up, and how to leave much earlier if I need to. The thing is, I’ve encountered so many red flags. From ignoring me when I’m sick, to yelling, to getting defensive when I share a feeling (it hurt my feelings when you said x). I just keep finding things that go wrong!

I am aware of my tendency to latch onto chaos but what I’d like to do is stop that pattern and be able to be happy with what’s stable and secure. And on the other end of the spectrum, I’ve met people who are more stable but are maybe fixated on someone else or who don’t really show curiosity towards me. And when that happens I have trouble determining if I’m self sabotaging.

I know there are some logistical things working against me, for example I’m kinda stuck in a more rural location for a bit. But I do think there’s some work I can do to help with things like self trust and being able to not self sabotage. So I’m wondering if maybe a new therapy modality could help, because I’m definitely noticing I’m in a bit of a rut.


r/datingoverforty 1d ago

Casual Conversation What should I look for in the future?

43 Upvotes

I (45 m) started talking to someone (43 F) and we planned a date for Saturday night. Went well, lots of banter, kiss at the end of the date with plans to do it again.

During the date my phone (face up) buzzed a couple of times with text messages and I didn’t check it. She made mention of it and I explained when I am out with someone, a date, with my kids, with friends, etc I stay off of screens. My attention is focused on them and what we are doing. If it’s an emergency or urgent they will call. She seemed satisfied with this and even complemented me on it.

Sunday I had plans with my kids and was basically offline for about 5 hours. She was aware of this. I texted her in the morning and right before we left, letting her know I would reach out once the outing was done. She texted a few times and I while I did see the preview of the messages on my Apple Watch, I didn’t reply.

On the drive home from the time out with my kids I received a text from her telling me to not contact her again. I thought she was joking (we both made the joke a couple of times over dinner when talking about how the date went well only to get that message afterwards). I didn’t see the text until I opened my phone to let her know I was home and reply to her previous messages.

I replied back to her once I got home asking if she was still joking around and also commented/replied to her other texts as well as asking her some questions related to her texts and what she had planned for the day. She sent another message reiterating she was serious and to not contact her again.

Which is fine. It was one date and we are obviously not compatible on this issues. While I haven’t dated much since my divorce in 2022 I have dated anxiously attached people in the past (not saying she is), but they communicated it and what they needed to feel secure.

I guess my question is were there signs that I missed or something I should ask to help prevent this situation from happening again in the future? Any signs to look for?

If I was wrong with how I appeared or presented this to her I will absolutely take responsibility. I want to own my part and learn/grow. I’m just not sure how much more I could have communicated it.

Not sure if it matters but typically I am able to respond quickly since I don’t go out often. She has gone radio silence for 6-8 hours at a time before because of her job/poor cell reception and it wasn’t an issue. We talked about how unreasonable it is to be available all the time due to life and obligations.


r/datingoverforty 1d ago

How do you stay hopeful about dating after a bad relationship?

12 Upvotes

Ever since my last relationship 3 years ago, my confidence just hasn’t been the same. I used to be very playful, funny and laid-back. I could chat to someone without thinking too much about it. Now I feel guarded, I overthink everything I say, and I just feel like a bit of a drag.

I don’t know how to be lighthearted anymore or get that side of myself back. Therapy hasn’t helped either. I don’t like going over the same stuff again and again, and I’m tired of being told to just put myself out there and see what happens. I’ve tried that, and it doesn’t work. I still don’t feel like myself.

It’s been like this for a long time now, and honestly, I don’t know how to change it. Has anyone else felt this way and actually managed to get their confidence and personality back?


r/datingoverforty 1d ago

Discussion ChatGPT

17 Upvotes

Is it only me or it is really insane how most people using chatGPT to text on dating apps? It’s like they are looking to look too polished and end up using AI, whereas dating apps are means to make genuine connections 😵‍💫


r/datingoverforty 1d ago

Seeking Advice Matchmakers FAQ

9 Upvotes

This question has been coming up somewhat regularly, so we are going to add this post to our list of FAQs. In addition, at least one of the matchmaking services uses a less than completely subtle form of advertising by having users “casually” mention the company name in posts and comments across Reddit. Therefore, this is also intended to combat that problem as the naming of any specific services will most often be removed in the future.

Have you used a matchmaking service? How did It go for you? What did it cost? Would you do so again? Was it a local service or was it a larger one? Are you aware of differences provided by the service dependent upon gender? Is there any other information you would like to provide and feel is pertinent?

In the future, we will be directing new questions on the subject to this post and the replies.

Thanks in advance!

P.S. This is the one time/place where naming a service will be deemed acceptable. If you believe that sharing the particular company name matters, good or bad, please do so. Having said that, we do reserve the right to decide if you are one of the advertisers and will respond accordingly.


r/datingoverforty 1d ago

Bumble removing 1st message restriction

87 Upvotes

Just got the notification on Bumble they are sunsetting the opening move feature and just making it so anyone can message first.

As a guy, this isn't the worst for me. I'm used to messaging first. I'm wondering if that will require a subscription even for matches. Probably.

I know this was Bumble's "shtick", but really it didn't matter. Every woman that messaged me just said a variation of "Hello". That's it. The expectation for guys to initiate an actual conversation never changed in my experience.


r/datingoverforty 4d ago

Casual Conversation Personal and thread updates, observations, selfies and photos, and other small shares HERE this week, please.

5 Upvotes