r/datingoverfifty

60M. I had three first meetings this past weekend. By having multiple meetings in a short time I inadvertently started to compare them to each other. It is probably not fair to do that but sometimes your brain does what it wants right? When you are in the early stages of getting to know someone, does there current and future financial situation play factor? I think that if you are 60+, it starts to become a relevant topic with retirement looming.

All three ladies I met were about the same age, but it sounds like they have very different financial situations. I personally do not consider income when looking for a partner but I wonder if women do it, whether they admit to it or not.

Second question is that of lifestyle compatibility. A person with a low paying job and no retirement will live differently now and later in life compared to an educated professional with full retirement and/or a 401k. Does love conquer all, or is income a factor? Would a drastic difference income lead to some uncomfortable realities later?

I'm definitely using this method or something very similar

I'm blocking men that cross my boundaries. I'm deleting matches that show no effort.

It's very freeing and it really makes sense. There are certain things that just reveal that someone is not a match. So why keep contact?

I was 53 when my second marriage ended.

I thought I knew what I was doing. I'd been through divorce once before in my late thirties. I figured I had enough life experience to navigate it. I downloaded the apps within a few weeks, started going on dates, and told myself I was ready.

I wasn't. Not even close.

Five years later — after enough mistakes to fill a book, which I eventually did — here's what I wish someone had handed me on day one.

**1. You are not healed just because you are free.**

The liberation of finally being out of a bad marriage feels like readiness. It isn't. Most men jump into dating carrying everything from their marriages — the anger, the resentment, the unexamined patterns — and then wonder why they keep ending up in the same place with a different face across the table.

The work comes first. Not instead of living your life. But before you get serious with anyone new.

**2. The women you're meeting are completely different from what you expect.**

Post-fifty women are not looking for a provider or a rescuer. Most of them have their own money, their own lives, their own hard-won freedom — and they are fiercely protective of all of it. They don't need you. They're deciding whether they want you.

That's a fundamentally different dynamic than most of us are used to. And it requires you to show up differently — not with what you can provide, but with who you actually are.

**3. The apps will mess with your head if you let them.**

I went through phases where I had twelve conversations going simultaneously, scheduled five dates in a week, and came out the other side exhausted and no closer to anything real. The apps are designed to keep you engaged — not to help you find a partner.

Use them as a tool. Step off when you have enough genuine connections in play. Don't let the dopamine loop of matching and messaging substitute for actual human connection.

**4. Your attachment style is running the show whether you know it or not.**

I sent a birthday card signed with words that six dates hadn't earned yet. I over-texted. I pushed for certainty before anything had been established. I was operating from anxiety dressed up as enthusiasm — and the women I was dating could feel it even when they couldn't name it.

Understanding why you behave the way you do in early relationships — and what's actually driving it — changes everything. It's uncomfortable work. It's also the most useful thing you can do before dating seriously.

**5. Slow down.**

Every instinct after divorce pushes toward speed. You want to lock something down before it slips away. You've already lost time and the awareness of that sits in the background of every new connection, quietly creating pressure that has nothing to do with the woman in front of you.

That pressure is what kills promising connections faster than anything else.

The men who actually succeed at this — who build something real rather than repeating the same cycle — are the ones who slow down enough to do the internal work first. Who show up as themselves rather than as a performance of the man they think she wants.

It took me five years and more mistakes than I want to count to understand that.

I ended up writing most of this down because I couldn't find a book that talked about it honestly — not from a pickup artist angle, not from a clinical distance, but from someone actually in the middle of it who made the mistakes and did the work.

If anyone wants the link I'm happy to share it — just didn't want to lead with that. Mostly wanted to put this out there because I genuinely wish someone had said it to me.

Happy to answer questions or talk through any of this — it's a strange and specific kind of hard and most men go through it largely alone.

This guy I’m dating told me after a few weeks of dating that he’s going to visit a “friend” in Italy from Pa who he had a fling with years ago who recently got married. I feel very uncomfortable with this and it seems very odd that he’s going for a month to visit an old flame and her new husband. In my 55 years I’ve never heard of anything like this and I don’t visit old boyfriends. Why would he be dating only to tell the potential gf that he’s going away to visit another woman and her new husband?? I really like him and we have a great connection but this recent detail doesn’t sit well with me at all.

Is this a sign to run?

Please give feedback. TIA

TLDR

I found yet another profile saying "ask me anything". I finally decided to take one of those profiles on their offer. Here's what I sent:
*************************************************************

The Snail Assassin: You are granted immortality, but there is a single, immortal snail that is always slowly slithering toward you. If it touches you, you die instantly. What’s your strategy to deal with the snail?,

The Ghost Niche: If you were a ghost, what extremely specific, mildly inconvenient thing would you haunt?,

The Food Sensation: Would you rather be able to taste colors only when you're in a library, OR be able to hear cheese but it's always a faintly judgmental whisper?,

My answers:

Snail Assassin: I'd just put a Post-It note on the floor that says 'Snail: Do Not Cross.' Legally, it has to stop. I don't make the rules of mollusk law, I just enforce them.

Ghost Niche: I would haunt USB ports so people have to flip it three times instead of the standard two.

Food Sensation: Hear cheese, 100%. But I'm specifically cultivating a diet of only Mozzarella because I imagine it whispers like a golden retriever who just wants to be included. 'Hey. Hey. You're doing great. That's a nice cracker.' Whereas I just know Blue Cheese would sound like my passive-aggressive aunt criticizing my life choices from the fridge at 2 AM. 'Interesting outfit choice today.'

Should I (50F) expect a man to msg the day after hooking up (if it seemed very successful anyway)? If he doesnt, is that likely to mean its a ONS?

New to dating and just like to know what to expect. I kinda expected him just to msg and say hope you enjoyed the rest of your day or some such, at least given how well the hook-up date went, but I didnt hear anything. I dont mind either way but do men at this age expect women to check in? I won't msg him but that's my nature

I am 50M and meet a 53F. We had a coffee date and ended up talking for two hours. Exchanged numbers, and she texted me some clear indicators that she was interested. This was on a Friday morning. So I scheduled a date with her for the next night we were both free which was the following Wednesday. She was headed out of town for the weekend, and we exchanged a few texts about what we were up to. Nothing extend, just a few texts a day. I was looking forward to dinner with her on Wednesday so I could get a bit more info about compatibility. She seemed to move fast with texting.

Day of the date comes, and before I checked to confirm with her, she cancels on me, it was around lunch time telling me she had a family emergency. I was disappointed, partially because I have had several last minute cancelations lately and they never reschedule. Also because I don’t like last minute cancellations particularly for the early dates, it’s a turn off. But sometimes it’s not just an excuse, but a real emergency. I texted her that I hoped everything was ok and to let me know if she wanted to reschedule, and she told me next week.

I did not contact her again, really for several reasons. One, I don’t know whether this cancelation was a low confrontation exit, maybe she changed her mind about me, has someone else she was more interested in, or something she would rather do than go out with me came up. No way to know, I barely know this woman.

So Sunday rolls around and I get a text from her that was very complementary of me but saying the she expected me to pursue her more, like call and text her. Now I am a bit taken aback by this because, we have spent two hours together and I don’t know her, and she canceled our second date at the last minute. What did she expect of me? I was looking forward to getting to know her better, but how do I even know if I want to pursue her at this point? She also mentioned that she is a serial dater, and while I didn’t tell her this because at this point it didn’t really matter, but I am a parallel dater. I need to take it slower and see if I want to invest in someone before going all in after one date.

Now clearly this is an incompatibility between us, which is fine. But my question for the serial daters, is this a normal expectation? That a man is going to pursue you and invest emotionally after one two hour coffee date? To me that screams desperate and I am far from that. I have several first dates coming up and more in the queue because I am looking for my person here.

I will try to phrase this the best way I can.

I dated a woman mid 50s. She said since she went through menopause, her external vaginal tissue is overly tender in an unpleasant way. She is ok with penetrative intercourse but she said oral is uncomfortable to her.

She is on hormone replacement patches and she said that allows her to have penetrative sex but it did not help with her outer tissue making her receiving oral off the table.

So obviously I respected her preferences and did not suggest me performing oral on her.

Here is my dilemma (it’s not a deal breaker) but I love giving oral every once in a while.

Is this common for women over 50?

I’m a 51-year-old female in separated six years and divorced a year and a half. Starting to look to date more in earnest. I don’t dress up for dates but I shower. i’ve been on three dates in the past month and all have been dressed even more casually than I am. And the one today had body odor. Conversation is great and I liked him so I thought maybe he just got real busy and couldn’t shower. I asked what he had been up to and he said he was just doing errands and work stuff at home. For other people encountering this minimal effort. Because pickings are slim I’m inclined to give them a second chance. But it certainly a turn off anyone else had this experience?

OK - I'll try to keep this concise.

I am a well-preserved, beautiful, financially stable 50F who people say look 40. (toot toot but facts)

My husband died 3yrs ago unexpectedly. We have a 10 and 12y/o. While traumatized, I've done a TON of work on myself (trauma therapy/rehab/counseling) -` that horrible occurrence was a strange gift to find the healthy place (except for that terrible loss) that I am now. It made me a better mother and person, tragically. My love for my him will never go away, but I am ready for companionship.

After 2 pseudo too-soon "relationships" in the wild (one : DV, the other : total stifling attachment) I had a long period of celibacy/loneliness as I came to peace with my family's circumstances.

I finally joined Hinge on my psychiatrist's recommendation (!). I met a great guy - not over his ex - all the chemistry and desire - but he just couldn't leave her (he had a hx as a swinger - also noted). DONE. Also MANY false starts.

One day I responded to a like - let's call him J - and we started funny chatting. We hit it off. I got my balls up finally and asked if he wanted to take it off the app - we exchanged numbers. The day after, J was off Hinge, inexplicably. We texted, made plans, kinda stood me up, a blizzard intervened the next time, we texted again Feb 14 (no meeting yet), then texted on and off. (I learned later he had lost his job and wasn't able to deal w/ Hinge at that moment. Valid.)

Me or he would randomly reach out, we'd chat, it would die. I looked at it like I would approach a friend - what's up? Did your cat come back? Are you a furry? A little flirting.. etc etc we'd joke around, then not chat for a week.

ANYWAY he FINALLY asked to meet again - we did make it happen- 4x in last 10 days: lunch walk, yoga next day w/3hr car chat (G rated), then dog walk 2 days later w/ 4hr coffee date (G rated). We laughed, shared..Good stuff!

I reached out LAST night to say let's hang again I had a great time and mentioned I didn't have kids so we went rock climbing (I don't suck), ate some food, he worked an uber prepickup for an hour and we met up again and walked alllll around downtown. Sober, chit chatting fun. I let him drive me to the river but didn't invite him to my house, not ready for that.

Yesterday I was chatting with him before our hang and sent him a pic of a guy with an enormous funnel cake. He said "Is that your other boyfriend?" (....?!)

We hung out till 1am last night (G rated, tho he put his hand on my back in his car and we had a nice hug w/ a peck lol, I felt chemistry) ... So I followed at 11AM today with a "Hey! Such a fun hang last night—my forearms are feeling it today. You're a total pro, thanks for being patient with me. 🥰"... and await a reply... anything. It's 8pm and NOTHING.

AN ASIDE: We have talked about my husband's death, he knows, and returned a deeply personal story of a woman he had dated on and off who had killed herself out of nowhere. So we've shared some heavy sh*t, and acknowledged each other for doing it. It's all been quIte mature.
So my questions are these:

1. This on and off, not answer texts right away, is this normal? I'm rusty.. Am I missing something? I do want more, but not tryna be pushy or eager either. We've been chatting since mid Feb, 4 dates.
2. When can I expect J to kiss me? I am old fashioned but also the take charge type. If I still drank I'd probably have kissed him already. I could have leaned in last night but.....What to do? How does this work?
3. I get good results w/ J when I throw out a few times for a hang since obv as a working single mom I'm terribly busy and he recognized that (I see you ppl saying I should not even consider dating right now... consider the kids - yes they've been through lots of therapy.. but Connection/Love is one of our basic Human Needs - see Maslow's Hierarchy of Needs). I just want a little more engagement sometimes. I also know it's still early and I was in a committed relationship where I didn't need to contend w/this. HALP!

That's all for now. Please, esteemed Redditors, be gentle.

Thank you for attending my TED talk.

Hello, so I’ve been dating someone for maybe a month or so. She is divorced a year after 25 years married. We had numerous dinner, movie, walking dates before any physical contact aside from a peck on lips in parking lot after dinner. The last 3 dates have been at our homes. We “kissed” after the first one where it was more closed mouth quick kisses.

The next date I said should we do the awkward first kiss. She thought we had already had the awkward first kiss and last time she thought i wasn’t kissing her back. So we kissed again and held closed mouth kisses longer. I was affectionate and was rubbing her arm and playing with her hair and putting my hand on hers. I tried to use some tongue and she just kept her mouth closed. She didn’t touch me back at all.

Last night was the same thing. No touch back, no open mouth kissing. I have been super patient after maybe 10 dates. I’m not trying to push her into sex but I’ve haven’t kissed like this since before 13 years old. No one I’ve been with or kissed did not open mouth kiss. Also I don’t think I’ve ever been on 10 dates with someone and not had sex. She doesn’t even touch me. I compliment her and tell her she is beautiful and pretty. She rarely responds, she never says anything about liking me or compliments me. The only thing she has said is she likes my glasses. She is Catholic and goes to church semi-regularly. She has asked whether I was talking to anyone else or on dating apps. I told her no which is true which leads me to believe she likes me.

I suspect it’s her nature, religion, upbringing, past trauma from marriage? I am thinking about asking about kissing preferences. It’s just very frustrating and I am affectionate and love intimacy and I just don’t know if she will ever be affectionate, complimentary or will have normal sex. Maybe that was missing from her marriage.

She had many great qualities and I live in a small town with few quality available people so I don’t want to give up on it but I’m concerned. Thoughts?

55f. Divorced almost 4 years after a 30 year marriage. Totally open to dating, but I’m perfectly content alone. That said, show me a kind man with a big sexy brain and their appearance (excluding hygiene) isn’t necessarily that important. Am I in the minority?

So many men and women our age prioritized spouses, kids, careers, aging parents and Lord knows what else, that we didn’t notice we were last on a very long list.

Our bodies represent the lives we have lived. Why is finding grace in that fact so difficult for us to give and accept?

Am I the hottest thing in shoe leather? Nope. But I’ve worked hard on myself and am pretty flippin happy mentally and physically. I like what I see and who I am. I know my worth and it’s not tied to the elasticity of my skin.

Before y’all come at me, this is just my perspective and I know you can’t paint everyone with a broad stroke. I’m just curious. Are you all about physical appearance? In it for the hook ups? Looking for “The One”? Given up? Content on your own?

Smoking marijuana, turn off or no big deal?

Just a heads up to the ladies in the group. There are men in our age group that start long term, text you every day, have many dates with you and in two months they send a text after flaking for a week: met someone next to home, are you looking long term or just fun? I still want to see you..​​

Do not settle up for less and move on.

My friend (I promise it is not me 😂) has her youngest son about to graduate from high school and leave for college. She has been married for 21 years and alluded to the fact that she put so much effort into the kids that she is not sure about the marriage anymore.

I know this term can result from many issues (infidelity, addiction,etc.) but did anyone divorce to empty nest issues?

So following on from my previous post, I’ve now got 3 other men who have already asked to meet after just one day of message on the app. So from all the other responses this is not a red flag I’m learning. Also I’m standing firm on the phone number I’ve had another one also ask for that but have said not until we meet.

There is also request for date from guy whose wife died in September I’m not sure about that one he didn’t have it on his profile but his first response to me told me about this said he would take things slow if I wanted but also was asking straight away for a date this week. If I accept all I will have 4 men on the go during one week or so , I guess this is modern dating ! How to then filter them out ?

So, is it that people our age just stay home? I refuse to do that! I don’t want to be a shut in. I want to go out and meet someone but I spent an ENTIRE day out and about, hanging at bars (watching Chelsea lose) and not one person spoke to me. What the hell? Am I hideous? Unapproachable? RBF? I have no idea but everyone else looked like they were having so much fun! Philly is super fun on a Saturday evening and I was all alone. But I’m happy for everyone else, sincerely. Live your life, guys!! We only have one life to live so love, laugh, get laid, and get out of your homes!

I’m 51F. My husband and I split up this December after I learned he had a secret girlfriend. The marriage had been over for many years so it ended now feels like a relief and I’m much happier.

I’ve recently started OLD and I’m finding that I’m not attracted to anyone I’m meeting. I’ve been on like 8 in-person dates and I’m not interested in any of them.

The only attraction I’ve had since my marriage ended was a short fling I had with a 27yo which was absolutely amazing. But it’s since fizzled and I don’t think something like that is likely to come along that often or be likely to last long.

I’m just reflecting on all of these dates and wondering about the future. I don’t think I’m dating too soon after my marriage ending because it was already over so long. So I don’t think that’s the issue. I know we all age but so many of these men seem to be overweight with yellow teeth 😩 I don’t want to be shallow but physical attraction is very important to me. I’ll also say that I’m very independent and don’t “need” a partner — it’s more that it would be nice to have sex again and have someone to do things with.

Just venting and sharing I guess. Does attraction change at this age? Are my expectations unrealistic?

I (58m) am bald and been that way for about 30 years. Our society is okay with bald men. There doesn’t seem to be any discrimination against bald guys in careers or day today life. I love being bald and I’m very proud of it. It’s practical, inexpensive and clean.

However, I did some research and I saw that only about 10% of women like bald guys. This is very bad for us from a dating app perspective.

What it means is that we are only catching 10% of all the right swipes.

Given that most men in general don’t get a lot of likes to start with. I find it extremely disadvantageous to be bald from a dating perspective.

I find this very disturbing and I’m looking into a hairpiece or toupee. If we miss the right swipe, we simply don’t get a second chance. On the other hand, a right swipe could lead to a date and maybe even a soulmate.

Whatever our dating intentions are, we could accomplish whatever we want as long as we catch the right swipe. Obviously, this does address short term dating challenges. Long term, let’s say we found a soulmate, it should be possible to explain the logic. For the soulmate scenario, we could trash the toupee. What do you think?

Hello, I went on two dates with a guy 58 years old, who’s lost his wife to cancer four months ago. I think we had two great dates but I’ve realized my perception is often not accurate, judging by the way others react.

So, this guy sent me a text today, after 6 days of our second date- stating that he was going to be busy with his wife’s memorial and work and that when he was ready to date again, he’d reach out to me. I replied this:

Thank you for letting me know. I really enjoyed our date too. I understand, and I wish you well with everything you have coming up.

After I sent, I deleted the conversation and his contact number.

I have two questions and one favor:

1. Do you think he’ll reach out in the future or this was a sift exit?
2. Do you think my response was ok?

Favor: do not judge me for dating someone who’s lost a partner after so little time. I have learned my lesson already