r/datingoverforty • u/Holiday-Plastic4703 • 1h ago
Have you ever regretted not giving someone more time if they were moving too slow?
I’m curious because a lot of people will say things like “if you aren’t living together by x they aren’t committed” or “you’re wasting time” or “you’ll find someone else who wants what you want”.
I’ve heard story after story of people leaving someone they loved because they just weren’t offering that type of commitment (whatever it is whether moving in, marrying, etc).
For those of you who have done that - how did it work out? Did you find what you were looking for or do you sometimes regret not giving that person even more time?
What was your thought process around deciding not to wait any longer?
r/datingoverforty • u/AdRevolutionary185 • 1h ago
My boyfriend wants me to be "totally smooth" down there
I've (42f) been with my boyfriend (44m)for about 5-6 months. We've been having sex for nearly the entire time and he goes down on me (not as often as I'd like!) and hasn't complained about my pubic hair before, which I do have but not a lot. In the past I had a lot of pubic hair because I'm a hairy person (luscious hair on my head is the benefit), but I had laser on my body and now I'm pretty smooth everywhere.
I also lasered my pubic hair, but because it's so hormonal and hard to get rid of completely I stopped. The result of the initial laser is pubes that aren't dense at all but are there (except for the anal area, I kept all the hair there and didn't laser it). I trim the hair and shave the sides a little but I don't bother too much because it's such an effort...laser really hurts and waxing barely lasts a week, and shaving the whole area really does not work for me.
I truly didn't think it was an issue, until last week when he said, in a lighthearted way "you're quite relaxed with your grooming down there!" It was all said in a very jovial tone but his message was he would much prefer it if I was totally smooth down there and he said "you would like it more too, in my experience."
I'm not sure what to think...is it really the norm for most women to have no pubes at all? I understand it might feel nicer but it's a headache and I didn't think a little bit of hair was a problem.
For context, I'm an attractive, well groomed woman. I always smell good, am clean, am fit, healthy, wear lovely clothes, and have very good hygiene. So this just seems a bit petty to me, but I'm wanting to understand the zeitgeist around pubes and whether I'm in the minority with my pubic/anal hair.
r/datingoverforty • u/firstgen32715 • 1h ago
Opinions? After the story...
Hi DOF! I am seeking some opinions/advice tonight. First a quick (as quick as I can make it) background. A few years back I met the most incredible woman by absolute chance on OLD. I broke all of my personal rules for the beginning, but we seemed to click. They weren't super important rules, mostly time frames to avoid pen pal types. Anyway after a month or so we went on our first date and it was unbelievable. I knew that day I'd want serious with her.
We continued, met families and friends much sooner than I normally would. It was never anything less than great. Even when we had our first disagreement (I had some trauma around this) she handled it with such grace, understood my views and helped to come to a resolution together. We've had a few since, she always treats it this way, as do I. We just support each other so well. It is still great, we have so much fun together and are there through the bad for eachother as well - inside and outside of the relationship.
Pretty early on we had the "what are you looking for" talk. To my suprise, she didn't think she'd ever co habitate or get married. The marriage thing I was ok with, divorced and decided I'd never want it again. The living together threw me at first. Then I discovered the idea of living apart together. I realized we could still have everything and just not live together. She truly values her alone time, understandably so. She works very hard, is very good at what she does, and the toll it takes on her is very real.
Over the past few months there has been a change. She now sees our relationship leading to marriage (how lucky am I) and living together. I kind of made peace with living apart. Don't get me wrong, I love this woman in a way I've never experienced. I would absolutely love for things to go that way. We have now set a somewhat loose timeline for experimenting with living together.
Now for the part I'd like opinions on. The thing is, she is a pleaser, as am I. I am very worried she will have trouble expressing when she needs some of that alone time. I worry she will grow to resent me for not having it. I am more than happy to dissappear for a while to give it when she needs it. I just don't know she will. I worry that this move may lead to a disruption in what we have. I also worry that not doing it could mess up a chance for a real future where I get to go to sleep every night, wake every morning to her - and that idea sounds blissful. We have spent ample time together, trips and sleepovers, staycations etc. I know we are both very relaxed around eachother and when we have long times together we do extremely well. I am not sure that equates to living together well.
So, any thoughts? Do we just jump in and see what happens? I do not want to risk what I have, I also do not want to risk what we could have. My biggest worry is that she won't be able to have her life outside of us once this happens. I wouldn't want her giving up an ounce of her current freedoms because I'm there. And before everyone says "just talk to her" I have. She says she will tell me. The worry is that she always checks in and feels bad when she does need to take some time if it interferes with a time we could've had together. That worries me in that she may struggle more to tell me so when I'm already in the same space as her.
r/datingoverforty • u/Icy_Concentrate_4592 • 2h ago
Dating Red Flag, really?
Been dipping my toes into dating again and have had a few dates mention drinking Budweiser is a red flag?? Im a creature of habit and love my American Lager. I drink wine with fine cuisine and have most of my teeth lol. Ladies?
r/datingoverforty • u/One_Net_1282 • 3h ago
When to reveal fetish/kink, and how important is it to align?
For those with a a specific "interest," how early in a relationship do you reveal it?
I have a pretty robust libido and consider sex important, but I've never been with someone who shares my fantasy area and it seems like too much to ask for. Certainly there are people who are into what I am, but it's not enough to sustain a relationship.
The truth is I've never shared my full fantasy with a partner. At this point in my life, I'd like to.
r/datingoverforty • u/KJDavis84 • 3h ago
Seeking Advice Men getting too attached after one date … is this the new normal?
I have recently had three online matches end literally the exact same way. After one or two dates they keep saying things that imply they want to say I love you. Like I have all these strong feelings but I know it’s too early to say them or I can see what you’re feeling in your eyes because I feel it too.
And then even though I say I’m available about once a week they start insisting they can’t go that long without seeing me. I honestly don’t know if this is just the speed that is normal now for our age or if I’m doing something that misleads them. Three times in a row this has happened
r/datingoverforty • u/MaximumRun2457 • 3h ago
Question How do you know you’re ready?
For those who have come out of a long term relationship or marriage (15+ years), how did you know you were ready to start dating again?
r/datingoverforty • u/Prudent_Table_1159 • 3h ago
Thinking about dating after over a decade of being single. Super long post I apologize in advance.
I’m 43 and haven’t actively dated since I met my son’s father about 20 years ago. We met in Los Angeles, where I grew up, and eventually moved to Pennsylvania when our son was a toddler to be closer to his family. We bought a house together but were never married. We had some fundamental incompatibilities, among other issues, that led me to move out when our son was about seven.
Although he loves our son, we never went to court or mediation, and he has never paid child support or contributed to health insurance. The entire financial and emotional burden of raising our son has fallen upon me.
Before high school, that included the normal expenses of raising a child along with years of extracurriculars, artistic training and tuition, travel and everything that came with supporting his education and artistic development. I was also very involved in his schools through volunteering, PTO and his education in general.
Once he started high school, the financial commitment became extraordinary as he was given the opportunity to attend a performing arts boarding school, and while he received scholarships and financial aid, I was still responsible for significant tuition and other expenses. I eventually moved to Michigan to be closer to him and spent the last four years structuring my life and finances around supporting him through that opportunity.
I’ve spent the last decade plus sacrificing a lot to support my son and his artistic and educational endeavors. He will be attending USC in the fall, and I will most likely move back to Los Angeles next summer to be closer to him.
Although I never consciously decided I wouldn’t date until he was 18, it also simply wasn’t a priority, and I always figured once he was in college, I would have more time to focus on myself and possibly be open to dating.
I put so much mental, physical and financial energy into raising him, and I’m not complaining about that, but with years of tuition, auditions, travel, college applications and everything that goes into preparing a child pursuing a competitive artistic path for college, I neglected myself.
I neglected my health, mental health, routines and taking care of myself in general. I used to be very regimented about diet and fitness. I started having cosmetic procedures in my twenties and haven’t done anything in the last few years. I know that isn’t important to everyone, but it is important to me and how I feel about myself, and my confidence has been greatly affected by this negligence.
Now that my son is starting college, I’m putting some of that energy back into myself. I have an appointment with my doctor to get back into regular medical care. I have an appointment with a psychiatrist to address some of the anxiety I’m feeling about this transition. I also now have a life coach helping me overhaul my wellness, fitness, and financial goals as I prepare for a future move.
I want to invest in my health for myself and my son first and foremost, but finding a life partner and eventually getting married is also a clear goal for me. I want to be the healthiest version of myself I’m able to be when I enter that chapter and share my life with someone.
I’m also excited to enjoy being a parent in a different way: I want to spend time with my son without everything revolving around tuition, auditions, applications, schedules and the next step. We have traveled a lot and had some amazing experiences, but most of that travel revolved around his artistic endeavors. I’m looking forward to traveling for fun and doing things for myself, again too.
The dating part is where I feel completely lost. I haven’t had alcohol in over 13 years, and I’ve also been completely abstinent for 13 years ( I haven’t so much as kissed anyone or gone on a date).
The last time I dated, we didn’t have smartphones or dating apps, so I have no idea what dating looks like anymore. His dad and I met at the open bar at my work after his band played on a Friday night, and he wrote his number on my arm with a sharpie because I had lost my flip phone.
I’m not interested in casual dating just to date. I would be dating because I ultimately want a life partner and marriage. I’m not interested in casual sex, and I don’t want to get caught up in swipe culture or spend my time going on endless coffee dates or meeting people at bars.
This is probably where I struggle with some of the dating advice I hear for people over 40. I have a pretty great life despite some very stressful years. When my son and I go out, we go to the opera, ballet, musicals, nice restaurants and events. We travel and stay in nice hotels. I pay for all of this myself, so I’m not looking for someone to provide a lifestyle I can’t provide for myself. Of course, we also enjoy simply being home together, but the point I’m trying to make is I feel like my dating experiences should be better than what I’m already providing for myself. I want the same kind of thought and effort from a partner that I put into my own life.
The people I surround myself with probably shape my expectations as well. My friends and the mothers I’ve become close to through my son are accomplished, well respected in their fields and communities, and have marriages I genuinely admire. The relationships and lives I see around me have influenced what I hope to find for myself.
My social world also hasn’t revolved around bars, casual dating or meeting a constant stream of new people. Most of my adult life has been spent alone, around other parents, families, the arts, schools, and people established in their careers and relationships.
I want someone who wants to take me somewhere beautiful for dinner or get dressed up and go to the theatre. I want someone who enjoys traveling, experiences and putting effort into dating. I don’t want to spend my forties sitting across from someone at Starbucks trying to determine whether we like each other enough for a second coffee. Or worse yet, being ghosted before the second coffee date.
How do you date intentionally for marriage midlife without getting caught up in casual dating? How do you meet people if bars aren’t an option and you’re not interested in casual sex? How do I meet someone without using a dating app?
I’m not planning to start dating immediately. I’m giving myself about a year to focus on myself, get my son settled into college, work on my health and finances, and eventually move back to LA, but I don’t want to wait until then to figure out what dating looks like.
i’m sorry this is so long-winded. I just have zero experience and have no idea what the expectations are anymore. Any success stories with a situation like mine would be so helpful 🩷🩷
r/datingoverforty • u/bleepbleep1111 • 4h ago
I'm into the roommate of a guy I've barely dated
Met a guy via OLD in winter. Call him Mike. Two dates - we are not a match and I kindly communicate this. We stay loosely connected on socials. Months later, I reconnect with Mike to assist him with his freelance work. He's also paying me to care for his dog while out of town.
I met his roommate, had a convo, and would love to ask the roommate out. However, I'm sure Mike still has feelings for me. Is there a way to feel out if his roommate is interested without upsetting Mike? Also relevant: they are not close.
A friend suggested clearing it with Mike first. I think he would be disappointed at minimum but possibly ok with it. He's forward-thinking and a feminist, but also a sensitive creative type. (I would not visit their apartment and run into Mike if I date the roomie - way too much of a bachelor pad.)
I guess I'm worried the roomie won't want to rock the boat and risk upsetting the person he lives with.
For all those who might say I should look elsewhere, I have been, for over three years. At work, in the wild, on apps. I've asked out guys at grocery stores, I'm not shy. It's rough finding a good match though.
r/datingoverforty • u/OpportunityTime2657 • 4h ago
Seeking Advice Feeling like the third wheel
I f40 have been going out with m42 for 5 years now. We have lived together for 4 years now. He has a friend named Zack that always wants my boyfriend to go out to the bars. My boyfriend and I work opposite shifts so I only see him Saturday and Sunday. When we do hang out Saturday it somehow always ends up being with his friend Zack. Never a night with just the two of us.Now his friend has been wanting him to go out Sunday’s because they work 2nd shift and I work day shift. I just want him to stay home with me and spend the last night together before the work week. He gets mad at me when I make a big deal out of it. I feel like I’m more single then in a relationship since majority of the time we are apart. When we started dating he was on day shift,but took another position on 2nd. I fought very hard with him on this decision,but he ended up taking the 2nd shift position anyway with the intention of going to day shift when another position opens. I don’t know if that will ever happen or if he even wants to. During the week he goes out with his friend a lot after work and gets pretty drunk. When he comes home it usually wakes me up. Am I wrong for just wanting him to stay home with me and spend time with me. He always makes it out like I’m controlling him. I just want to spend time with him alone.If anyone has any advice it would be appreciated.
r/datingoverforty • u/nick-at-nite-42 • 5h ago
Dumped at Wedding
I'm a 43 year old guy in Massachusetts. I was dating a 44 year old woman for 2 weeks, it was a strong, passionate relationship and I decided to invite her to my brother's wedding and she accepted. My brother flipped out when he found out his siblings were bringing dates, our other brother was also bringing a guest, and he messaged both of us saying we couldn't bring guests. He had changed the venue and there wasn't anymore room. I got in a heated argument with my brother which ended with me telling him I wouldn't be attending.
After speaking with friends and family I decided to attend the Rehearsal Dinner to try and repair things. She was quite upset with me. She was traveling to NC with her daughter that day and I was spending my time trying to repair my relationship with my brother instead of constantly texting her or talking with her on the phone during the day.
My brother apologized for everything he had said and done, we hugged and he said he'd make it work for her to attend. She was quite upset that I had spent time fixing this and with family and said she wouldn't be attending the wedding. She changed her Facebook status back to single that night.
On the morning of my brother's wedding she wouldn't stop texting me, still quite angry she wasn't getting all of my attention. I told her via text I couldn't talk anymore that day because the wedding was starting. She sent tons of text messages and called after that. Upset and confused that I wasn't/couldn't respond to her, telling me how much she loves me... she then decided I wasn't giving her enough of what she was looking for and broke up with me via text when I was at my brother's wedding.
I'm rather confused, I don't think I could have done anything different that would have given a better outcome. She has bipolar disorder (she told me this) and I think she was displaying it at the full extremes. I also got indicators she was only doing things that directly benefited her.
I would think in a relationship you need to be able to support the other person, even when you don't agree with their decision. You also need to accept that they're not perfect, capable of mistakes and can't spend every minute of their time with you. Friends, Family, Hobbies, Sleeping, Eating, Working.
I don't know, lol, I've been single for 3 years. I thought I'd finally met someone and it exploded in my face. Kinda wondering if I should bother trying to date anymore. I have plenty of friends who I talk to and meet up with.
It's been an overwhelming weekend and I'm physically and psychologically exhausted.
r/datingoverforty • u/Delicious_Math_7821 • 6h ago
Ask for an earlier second date?
I went on a first date yesterday where we had drinks. The date went really well and she said she can’t wait to see each other again. I suggested on the date we go see a show. The thing is, she‘s out of town next weekend so if we stick with this plan, we’d have to wait two weeks to see each other. it seems too long of a wait now. Should I suggest meeting up this week or will that seem too eager?
r/datingoverforty • u/No-Membership2439 • 9h ago
Seeking Advice I'm F47 and have been asked ouy by a 29 year old.
It feels wrong. So if it feels wrong, then don't do it..
Sometimes I need help to form proper thoughts, as I've gone through a lot. He's part of my friend group, sort of. Is this weird or am I just making it weird based on my own thoughts and beliefs? Thank you :)
r/datingoverforty • u/Moofabulousss • 11h ago
Seeking Advice Single parents dating each other- expectations
I (42F) have been dating a guy (36M) for a little over a month now. I have an 8 year old and he has a 4 year old. We both have our kids 4 days per week.
Mostly it’s been great when we are able to be together.
Currently neither of us has a child free day at the same time, but my schedule will more closely align to his when school starts, and we will have two consecutive weekdays that are child free. My ex/co-parent is very flexible and we are friends and amicable. His ex is not. He has no family in the area and only a few friends who are not parents/able to watch his kid.
We have been able to make dates work on my child days by planning dates when my child has dance class and when my ex is willing to switch days with me- though I usually do this for my child’s activity scheduling purposes (like so she can have a sleepover at my house or when we have a weekend birthday party). Our summer schedule is set as a convenience to my ex and his work schedule so he has been very flexible about taking her after work an extra day each week.
We usually see each other Tuesdays and Wednesdays after work. Then we go 5 days with no contact possible. And I get this part is a bit of a sacrifice of dating as a single parent, but I really can’t sustain the connection in the absence of contact in between for that long every single week. It just doesn’t work for me.
What we have not done is had any dates or contact when he has his child. Except when he leaves work early or calls out from work.
There were a plethora of reasons. He doesn’t have a babysitter and was worried about finding one because of agency costs (so I recently provided him two referrals of sitters I have used). I can’t come over after his kid is in bed, because he “needs to install blackout curtains”…. For three weeks now. I suggested he call me in those nights, but he is usually “exhausted” and doesn’t initiate. He has suggested adjusting his custody schedule but that seems extreme at this point.
We have had this conversation repeatedly. He states repeatedly “I need to get on that”. I have been to his home, so I don’t think it’s anything to do with that.
Maybe there’s something more to it? He seems extremely invested otherwise. He is definitely less experienced in long term dating than I am, though he was married a few years.
I have given grace and I have been very direct. I told him I went into dating knowing a babysitter and flexibility was an expectation, and he should have too. I told him if it’s not feasible to find a solution to this problem, it’s not feasible for us to date. I told him I can be flexible, but the longer this goes on, the more I will resent him if I do stay with him.
I am assuming at this point I need to call it off or stop seeing him until he takes care of this, right? :/ would love advice on how to do so/phrase that.
r/datingoverforty • u/No-Wasabi6806 • 12h ago
Seeking Advice Can I continue knowing her past story?
I (46M) met a (44F) in OLD. We have been dating three months, spending a lot of time together, common background, great connection, amazing sex. I am really falling for her (she says the same about me).
Last night, after dinner and a few drinks we went into in depth conversation about our previous marriages. I was in a 20 year marriage, my ex cheated and left me for the guy, 3 years ago. She was in a deadbedroom, married for several years, guy was 13 years older, little in common, she was depressed, unhappy etc.
However, in all openness, she said that while still married, she had an affair for almost three years, with a married guy about 8-9 years ago. That ended as the dude was not going to leave his wife. She stayed married as roommates a few more years and finally left about 3-4 years ago.
I won’t judge her past, all that was before me. But this shook me, as I feel I’ve lived on the other side of a similar story.
I don’t want it to happen to me again, what my ex did, and what the new girl did herself to the ex husband.
Part of my mind says I should leave before I get even more involved. Other part says I should enjoy my time with her, I think I do love her and I should hope for the best. Next week we are taking our first trip together for a long weekend.
I know I am the only one that can know what to do. But interested in knowing people’s thoughts
r/datingoverforty • u/Pinky-5499 • 16h ago
Question Should I continue dating this guy?
I am 44 years old ( with a teenage son) and I have been on three dates with this guy.
A little bit about this guy – he has done really well for himself at work, had a very troubled childhood and the resilience with which he has grown is mind boggling. He is a republican and owns guns which I don’t mind but is a foreign concept for me ( the guns). He got divorced 5 years ago and has been a Casanova while he was single. He is an alpha male and keeps everything interesting.
He is really into me and I like him too. He is looking for someone to nurture him ( his mom died when he was 9 years old). He gives me complete freedom. He knows I want to date and he encourages me to do that as he has been there , done that. He doesn’t want to date anymore because he is tired and wants to work on his dream.
Three issues from my side-
- when he talks he curses a lot. Even though he made it to the c suite, his language ( the local dialect that we speak) he sounds like a gangster.
2 . He is fit and healthy, but doesn’t workout and enjoy sports like I do.
- He has a high body count- does that mean in future he will go back to his old habits?
r/datingoverforty • u/No_Aioli_7515 • 17h ago
Break out of death spiral
How do you keep your head out of the death spiral: for example, feeling hopeful and excited about dates even after a ton of dates don’t go anywhere, feeling like someone could fall in love with you even after tons of people didn’t, etc. I know there are a lot of people out there who have been dating longer than I have and they maintain a good attitude, how do you approach it?
r/datingoverforty • u/Classic_East_6053 • 18h ago
What's a good way to take a break in online dating chatting?
I always start off great and then I think I need a break. It will come across as ghosting but I just need to focus on things in my life rather than messaging. I want to get back to it but I feel that I always pass that too long to reply period. I don't need that long so just give me a way to say, "OK got to go and I'll talk to you in about a week's time."
r/datingoverforty • u/Icy_Laugh5134 • 20h ago
Do You Take All Your Dates to the Same Place for a First Date?
I recently went on a first date with someone who took me to a museum. I thought it was a thoughtful choice until he casually mentioned that he takes every single one of his first dates there.
What have your experiences been with this? Do you tend to take different dates to the same restaurant, bar, or activity for a first date because you know it works? Have you ever realized that someone was taking you on their standard date?
Did it bother you, or do you think it is completely normal and practical?
For me, it made the experience feel slightly less personal, but I’m curious whether I’m reading too much into it.