r/datingadvice

30M, will be 31 in January which is insane lol. Not an excuse but 10 years ago in college I started to get anxiety and I’ve been battling an anxiety disorder ever since. I’m actively trying to recover now, but I haven’t dated. Like at all. No experience. I guess I was just trying to survive the last 10 years. I have a good career I would say and I’d consider myself a pretty good looking guy and have been told so. On the shorter side but not drastic like 5 9. I would say I used to be really introverted but I have pushed myself throughout my 20s as well. I’d say the last several years I’ve pushed myself to approach women out at bars with friends and such. I got a few numbers but it never went anywhere. Dating apps, maybe I’m too picky on there, but I never have any luck and I can’t be bothered anymore. My likes are not reciprocated and I just don’t get much activity at all. The most important thing for me right now is my mental health of course, but I also just can’t see any sort of avenue or a future with a woman at this point. Especially at 30 with no experience. Am I being harsh or this is a fair realization unfortunately?

It will be our 2nd date and so far I really like him. First date we met up for lunch and had such a great time we kept it going and went for ice cream and a walk. We had a nice kiss when he walked me to my car. That was last weekend and we’ve texted and/or talked on the phone every night since.

He invited me over tomorrow to his place, he’s cooking dinner. I don’t want to be naive if sex is implied in these situations. Would it be weird to ask him what his expectations are?

I’m conflicted and probably overthinking because I do like him and wouldn’t be totally opposed to hooking up, but I’m looking for more than just a hook up and would like a LTR ,so I don’t want to be put in a certain category. I’ve had experiences in the past of being intimate too early and feeling used after because things change up.

I guess I need to use my big girl words and just communicate, but I’m curious what is the general vibe is with this type of situation.

I feel exhausted, I have been feeling very out of the place lately and everyone around me is in a relationship or finding someone they like. I recently graduated n during my school days or graduation days I have found no one, I have been single my whole life. I am 23F and I don’t have a lot of friends and the ones I do are all female friends. I have had a few crushes here n there, I have had a few crushes here n there but they r always either in a relationship already or just not available. So I went online to search, n I finally pushed myself to go out on a date with this guy, he was almost an hour late, it was a horrible experience, I kept wondering if he even likes me or not by the end of the date. Nothing is working, nobody has a crush on me, neither do anyone likes me, I don’t have a lot of male friends either. I sometimes just wonder if I am doing anything wrong? I am very exhausted, seems like everyone is finding their love/soulmate other than me. Any help, advice or any comments would be helpful!! Thanks in advance.

Me and my ex were friends for 1 year and dated for 4 months within which we were extremely close. He broke up with me because he felt mentally unwell and didn't feel like he should be in a relationship. His reasoning was that he wanted to fix his issues alone and that he couldn't take care of himself let alone the relationship.

He was also moving 2 hours away by car and was scared of long distance since he hasn't done it before (I was his first girlfriend while he was my 3rd, I already did long distance before and it had worked out)

I was extremely sad after the break up and cried almost every night, I ended up begging to get back together but he was firm on his decision and told me that it would hurt him but I need to move on. We end up not messaging or seeing each other again.

One month later a friend introduces me to his roommate 21M and we get along quite well, we're both ambitions, nerdy and share similar interests. He ends up asking me out on a date and I said yes. The date went really well and the guy is really sweet and pretty too. I told him that I might not be ready for a relationship since I recently got out of one and need some time to get over it before I commit to anything else. He told me he was in the exact same situation, his ex broke up with him 2 months ago for similar reasons and he's ok with just going on dates now with the hope of potentially getting together.

At 5am after the date my ex texts me a long message saying he misses me and wants to get back together, he claims that he's gotten help for his issues and did a lot of thinking and realised that he wants me as his girlfriend. He is now ok with long distance and promises that he will put more effort into the relationship, he's now gotten a job as well.

So now I'm in a dilemma, do I get back together with the man I loved and still have some residual feelings for even though he might go back on his word and break up with me again or do I move on and start a fresh chapter with the new guy who is really sweet and relationship material but I don't have super strong feelings for yet since I don't know him that well.

So I didn’t date for years, usually just kept things casual and tried to bring woman to my place to smash. But now I’m 37 and Lately I’ve been trying to take women on dates, I get numbers often even approaching in person which people say nobody does anymore lol. But about 90% of the time they don’t text back, they make plans and flake, or they make it difficult to schedule a date. Is this just what modern dating has become or what? lol just curious

Me 32 female him 29 male. Just looking to see is this normal. Talking about a month and have had 4 dates. At the start we were sending big essays to each other and responding quick. Dates have gone well one had to be rescheduled due to work (he works in a high performance job). On the last date he asked me to meet again and this is planned however since that date there have been 5-7 hour delays sometimes without messages and dramatic length decrease. He has a very busy period in work and a lot of hobbies outside of work. Date 5 is still planned and I have asked is all ok and he has said yes just busy. Is this normal or am I being slow faded? Messages I receive aren’t very flirty but checking in on me updating me on things his side.

I've had a real attitude problem with being tested in dating and relationships as long as I can remember.

I can only see it from the intreptation that instead of the person having healthy trust in a stranger, and most importantly, time and patience to get to know another person on a natural pace and flow, they try to confirm their own negative expectations usually based on their previous experiences right away and it makes the whole thing feel more like an job interview with pass and fail instead of natural attraction and compability. It takes me out of my own element where instead of being allowed to be, are thrown into a situtation that is just unnecessary drama and since I know I am being tested I lose the mood simply from thinking okay this was going well until this point and what is that one behavior they are looking for that would be the fail and do I embody that or not and is it a deal breaker, because then the date is over and there is no future for a relationship. So usually when I notice I am being tested I fail on purpose with often satirical methods. Might as well make a memory out of it.

I just can't think the relationship would be anything else than finding myself being projected as someone I am not and I am guilty until proven otherwise an innocent person does not need a trial. It's making a problem when there was no problem and when my mind notices the expectation it just takes away from my serenity when I feel like I am made responsible for the contents of another person's own head and the only solution would be to prove myself not to be something I already am not - over the other person just being vulnerable, open and honest in their communication.

Now I'm closer to fourty than thirty, and I've had one long term relationship and that was with a woman who never tested me. That was from late teens to just about halfway to thirty. Ever since, I haven't been in a relationship, and one of the reasons is I find it a real compability issue to be tested. Did I actually meet the exception once, and then couldn't pass the rule? Is this an actual me problem? Or have I just met the wrong people after? Will the testing actually ever stop if I grind my teeth through it?

Recently, I have been talking to a guy that's been in my mutual circles for a couple months, but we just hardly crossed paths enough for us to have extended conversations one on one. It was always in group hangouts where I'd see him, we talked casually, but nothing serious. He is closer to my older sister, but not by much.

A while back, he walked me home in the evening after an event and we talked on the way, he was just really sweet and we were joking-flirting. He ended it with this weird thing where he put his hand forward, for what seemed like a handshake, but then turned my hand upwards and lightly squeezed it when I tried to shake it lmfao.

A week ago, we had a ceremony for grad, and an afterparty for anyone not in the major to join. He came up to me at the party and congratulated me.

We were having the funniest conversation. He was being flirty, and the whole time his eyes kept panning to my lips 😭 he danced with me, kept off another guy who got close to me at the party, asked me if I made it back safe.

Now here's what confuses me, it's only been me initiating texts. He doesn't text me at all, but when I initiate convos, he's rly sweet and responsive. And to top it off, I've just seen him with another girl out walking together and it didn't really seem friendly, but idk the context. Not my business, we're nowhere near exclusive, but idk why he'd keep flirting with me irl 🧐

Maybe I'm not a dating expert, but I feel like ik when someone is dragging me along. He's just giving mixed signals, I can't tell what he's trying to do. He seemed nice and is always respectful, maybe I read him wrong, idk.

P.S. we were both very very sober at the party, designated drivers and all 😭

TLDR; I'm Carrie minus the Manolo Blahniks

So I am aware I (38m) have an anxious attachment style, which I believe probably originated in childhood but was reinforced by an especially painful breakup 10 years ago (I was totally devoted and she blindsided and dumped me and moved on, refusing to ever speak to me again).

I've had a bit of a hard time with online dating. Like most men, I don't receive a ton of matches (maybe 15 a month), but I get enough that it's not totally useless. I only like women I'm genuinely interested in and attracted to, so I find that when matches do come through I'm quite happy with my results.

However, I have this pattern where things seem to go well on the first date, a woman agrees to a second (in many cases taking initiative to reach out to me after the date or take extra unnecessary steps to stay in contact when she could have let things fade), only to back out or ghost.

I think this pattern combined with my own relationship trauma and anxiety (and the relatively low number of matches) has made me hypervigilant about any hint of someone pulling away or losing interest in me. I also admittedly have somewhat low self esteem and poor self-image, so I find it hard to believe attractive women genuinely find me attractive sometimes. Basically I always assume if she doesn't want to see me again it's because I wasn't good looking enough.

Anyway, that's the context for my current situation.

I matched with a woman I felt pretty excited about. She's beautiful/my type, smart, cool, artsy, etc. Basically just seems like a catch/good fit for me. We had really great rapport over text before our first date, exchanging lots of messages with clear enthusiasm on both sides. Then we had our first date, and it seemed to go well. I told her I wanted to see her again and she said the same.

In the few days since, we've texted every day, multiple times, with lots of witty banter, a little flirting. She's often the first to initiate and she sends photos, voice notes etc. She clearly has some interest at least.

But the last day or two the messages slowed down / the messaging "day" ended much earlier. I know she has some family in town, so it's probably just that, but my anxiety is running wild. I know I shouldn't be so invested after just a first date but it felt like such a good fit and like things were going so well. It felt so good to have someone I was excited about seem excited about me. We have a penciled-in plan to see each other next week, but that anxiety is just telling me she's going to disappear any day.

So basically I need your help. Talk me off the ledge and help me avoid self-sabotaging, if it seems like this is all in my head. Or, if there does seem to be something to be worried about, let me know if I should brace for that.

I promise I'm not a creep/weirdo. Just somebody who's had a lot of bad experiences and been hurt but genuinely wants to find a lasting connection.

First of all, I am a bit conscious of making this post because it comes from an extremely vulnerable place, and I am trying to get as much information as possible on whether I should try something or it is time to just move on and completely forget about this girl.

We met in July, and had 4 amazing dates. After our 4th date, she asked to not see each other the following week because she was overwhelmed at work and needed to "catch up" in her free days. I gave her space and time, so I only communicated here and there for the rest of the week. At the week mark I messaged her and asked how things were and if she would like to go on another date, to what she agreed, so we saw each other and during this date we had a conversation where she expressed her being concerned of not having enough time to dedicate to the relationship and that she felt it would be unfair to me, as she did the same to someone she dated before, and did not want it to end the same way. I said that I understood and that I appreciated her telling me, I was open to taking a slower pace and see where things go as we both navigate busy schedules.

I deal with a full time job, part time job, and full time college. She dealt with three jobs, so we definitely had a lot going on.

Things start slowdown a bit, we decide to go to mass together one Sunday, then we hang out at a local place a few days later, and afterwards we had a two weeks "break", as she needed a week to catch up with work, and the week after her parents would be in town so she would also be unavailable. Fast forward, the two weeks pass, her parents leave so I ask her to see each other and we agree on a day, we meet, and I felt that "date" was rushed, as it only lasted one hour. Later that day I asked if I could see her again during the week to what she suggested we could do something the day after or the next day, I arranged something for the day after, I felt it was okay, I had to leave at a specific time to be at school, so I had set a specific time I'd be leaving at.

A few hours after the date I receive a message from her that basically explained that since she explained her scheduling issues, she had already a foot out the door, and that she was trying to make it work because of how wonderful I was, but that she felt it simply wasn't going to work and that we would be delaying the inevitable.

I respected her decision and said farewell.

However, although she never mentioned it, I knew for a fact that her schedule would get better by the end of this month, so I was willing to keep things slow. And I am now debating whether it is a good idea to reach out by then and try to give it another shot; I really liked this girl, and I would really want to at least give that a try and see if there is anything that can be recovered.

For anyone who's been in a similar situation, would you consider reaching out once the practical circumstances had changed, or would you take the other person's decision as final and not reopen the conversation? I'd appreciate honest perspectives, including reasons not to reach out.

I’m a female college sophomore, and I’ve developed a crush on a guy in one of my classes. We’re both somewhat socially anxious and reserved, so starting conversations has been difficult.

We first interacted when he asked me to send him an assignment. A little later, we were partnered for an exercise and bonded over both having social anxiety. That conversation felt surprisingly natural because he kept adding to it and telling me about himself. Since then, we’ve had several smaller interactions. We’ve sat together during class trips, although we usually end up scrolling on our phones instead of talking. We’ve also made small talk, exchanged looks when something funny happened, and developed a little playful banter. He has occasionally initiated by asking me questions about class, but most of our conversations have happened because the situation put us together.

He has told me that he isn’t very social and genuinely enjoys being alone. Once, I asked whether he minded me sitting beside him, and he said he would have told me if he didn’t want me there. On another trip, he chose to sit alone and explained that he simply prefers it sometimes, which I understand because I’m similar.

I recently found out that he had a girlfriend during our earlier interactions, but they broke up a few weeks ago. He never mentioned her, but we also weren’t close enough that I would necessarily expect him to. Because the breakup is recent, I don’t want to rush him or treat his being single as an opportunity I need to jump on immediately.

I’ve also become good friends with one of his close friends and the rest of their friend group. The mutual friend knows I like him. He doesn’t want to speak to the guy for me, which I completely understand, but he has offered advice and said he’ll help make conversation easier when we’re all together. He recently brought me along when he visited the guy’s dorm, but I was nervous and barely spoke.

The next day, I tried asking my crush about his major after class. He answered but immediately walked away. It was the end of class, so he may have simply needed to leave, but it made me worry that he was trying to escape the conversation. He also hasn’t added me back on social media, although he told me when we first met that he rarely adds people back.

I can’t tell whether he is shy, emotionally unavailable after his breakup, uninterested in me, or simply unaware that I’m trying to get to know him. I don’t want our mutual friend to play messenger, and I don’t want to manufacture encounters or become the girl who constantly follows him around. At the same time, I’m worried that if I completely stop initiating, nothing will ever happen because we’re both socially anxious.

Should I give him space and see whether he ever initiates, continue making occasional conversation in class, or eventually ask him directly if he wants to get coffee or food? How can I show interest without making him feel pressured—especially so soon after his breakup? What signs would tell me that he’s shy versus simply not interested?

TL;DR: I like a shy, recently single classmate who is friendly and playful when we naturally interact but rarely initiates or extends conversations. We share a close mutual friend, but I don’t want to use him as a messenger. How should I get to know my crush without chasing or pressuring him?

Hey guys. Me and this guy in uni had been talking and hanging out for like a week. Im 18F and hes 24M. Im very sure he liked me and i liked him a lot too. We talked about our age gap a lot and we were both very hesitant on it but liked each other. One day he just left me on delv for a full day and replied when he saw me walking by in campus and i avoided eye contact, then he texted me back amd said he was supwd busy with school (saw him hanging out with his friend earlier) so i replied and said “its okay i think its bettwr if we stop talking anyway” and he said “i agree take care”. I saw him on campus a couple of times after and he looked like he wanted to talk but i keep avoiding him. Should i text him? Or just leave it? We both had amazing chemistry. I keep holding back on asking him whethwr or not he had a problem with our age gap or there was another reason. Am i being too beg?

I’m so curious because I don’t know if it’s accidental, but sometimes I would catch him staring at me from a far and the other day we were both sitting down at dining tables far away from each other. We just kept eye contact and lokknh up at each other.

I'm 30 M and I've never had a girlfriend or even kissed a girl. I was in target and a beautiful girl started talking to me and gave me her number. I want to text her but I'm not sure if she will want to be with me because I have no experience dating. I think at this age she would expect me to know what to do in terms of dating and intimacy, so I don't know if this will work. Should I just delete her number?

I am not trying to establish that they are superficial or something. I am just trying to find a person who would love me for who I am. I act nice and respectful as earlier but it doesn't seem to work. This has started to make me feel terrible about myself and it's affecting my self esteem.

18M, I’ve never dated. The reason I’m asking for advice is because I accidentally made a life where I have barely any opportunity to even connect with women.

I’m intellectually gifted and because of that, I decided to choose incredibly advanced classes for my grade level because I needed the challenge to not get bored. But, it so happens that these said classes create like no opportunity to connect. Partially because some are online. And, my general social preferences lock me out of a lot of normal ways to meet people. I never hang out with anyone, I’m very introverted and anxious, I dislike social events or parties, I don’t have much of a social media presence, there aren’t really any clubs that interest me, I don’t have any social presence outside of school, my hobbies are solitary, etc. and probably the worst among all of my social limitations is that I cannot get myself to initiate conversation with women unless there is an absolutely clear reason to do so and haven’t been able to since I was 11… meaning, I cannot easily make small talk. This was fine for a while, but as I got into more and more advanced classes and had less forced contact, the amount of interactions I had with women slowly dwindled into basically nothing…

I’m not lonely in the usual sense. I have many male friends (10+). But my social network is exclusively male. And sometimes I think maybe I’m just so unattractive that women don’t even want to talk to me or look at me. But also, over the years, I’ve become socially avoidant… I don’t really hold eye contact, I avoid looking at women especially if I’m attracted to them, I definitely don’t approach them or show interest in any way, and I get very anxious around them. And that could definitely contribute.

And even when I did have connections with women in the past, I struggled heavily to deepen them because again, I couldn’t initiate conversation. So it was all dependent on her. If she decided for whatever reason to stop talking to me, the connection ended. If the school year ended, also, the connection ended. And if I put myself in her shoes, it makes complete sense why the connections wouldn’t deepen… I personally wouldn’t want to deepen a connection with someone who only responds and never initiates, only looks at me if I talk to them, and doesn’t show any interest in me.

The part that I hate about this is that it made me view women as romantic objects. Because I have such little contact with them, my brain can just ruminate endlessly and obsess. But I recognize that women don’t owe me anything and it’s their choice to not talk to me, even if it causes me pain.

A couple days ago I (F23) had a really good conversation with an employee at a store I was casually browsing. He started the conversation and we talked for 10-15 minutes about random stuff like our hobbies and interests, with an emphasis on my pursuit as an artist. Afterwards, he asked me my name, shook my hand, and introduced himself too. A while later, as I was leaving, he gave me a card and told me he wanted to be one of the first people to see my art once it's public.

Anyway, the card has his email and phone number on it. It's essentially a business card, although he wasn't trying to sell me anything. I've considered reaching out and saying smth like "hello, I had a great time chatting and would love to talk more if you're interested!", but I'm assuming he was only being nice and doesn't actually want me to contact him. I would love to chat with him more, even in a casual context, but if I make it weird I will never be able to show my face there again LOL

Any thoughts are appreciated. I've received very little male attention in my life so I'm pretty dense when it comes to interacting with men in any context lol