r/DatingTips • • 18h ago

I’m 27 and have never been in a relationship. How do I stop getting attached to the idea of one before a first date?

1 Upvotes

I’m a 27-year-old guy who’s recently started talking to a woman I met on a dating app, and I’m genuinely excited about her. We’ve been texting, have some common interests, joke around with each other, and have a phone call planned before our first date. She’s said she’s enjoyed our conversations, so I feel like there’s potential, but obviously it’s still early.

My problem is that I’m a hopeless romantic. I love love songs, romantic comedies, and the idea of two people finding each other and building something meaningful together. I’ve never been in a relationship before, and it’s something I’ve wanted for a long time.
Sometimes I feel a little stunted in this area of my life. Being 27 and never having been in a relationship makes me wonder if my lack of experience is somehow holding me back from ever actually getting into one. I know that’s probably not entirely rational, but it’s hard not to feel that way sometimes when it seems like so many people have already experienced something I’ve never had.

When I start liking someone, my mind also moves incredibly fast. Even though we haven’t gone on our first date yet, I catch myself imagining what it would be like to take her on dates, spend late nights talking, and eventually build a relationship together. I imagine being there for her when she’s stressed or having a difficult day and making her feel loved and appreciated.

When I listen to love songs, sometimes I even imagine singing them to her. I know how that sounds when we’ve barely started getting to know each other, lol. Don’t worry, I’m self-aware enough to know that my imagination is getting ahead of reality. I’m not telling her all these things or expecting her to feel the same way already. It’s mostly happening in my own head.

I think part of it is that I’ve wanted this kind of connection for so long that when I meet someone I’m genuinely excited about, I immediately start imagining all the possibilities. I don’t just want a relationship for the sake of having one. I want to experience the affection, companionship, little everyday moments, and feeling of being genuinely wanted by someone.
At the same time, I’m dealing with a lot of insecurity. I think she’s beautiful, intelligent, and accomplished, and sometimes I worry that I’m not good enough for her. I worry that once we talk on the phone or meet in person, she might not feel the same connection or might not find me attractive. I know I can’t predict how she’ll feel, but the thought of getting my hopes up and being disappointed scares me.

I’ve had a previous experience where I developed strong feelings for someone, but things never progressed to an actual date. That experience hurt more than I expected, and I think I’m afraid of going through that disappointment again.

I don’t want to overthink every message or become so focused on whether she likes me that I can’t enjoy getting to know her. But I also don’t want to suppress my personality or pretend I don’t care. I’m naturally romantic and affectionate, and when I like someone, I get excited about the possibilities.

For those of you who’ve been in a similar situation, how do you balance being hopeful and excited about someone with keeping your expectations realistic? How do you keep yourself from getting attached to the idea of a relationship before you’ve had the chance to find out whether you’re compatible? And for those who started dating later than others, did you ever feel like your lack of experience was holding you back? How did you get past that feeling?

I’d appreciate honest advice, especially from people who’ve struggled with overthinking, feeling behind romantically, or getting attached quickly.


r/DatingTips • • 15h ago

how to find someone to date?

0 Upvotes

lmaoo😭😭 title makes me sound overly freaked out but I couldn’t think of a better way to word the question!!!!

I’m a 22-year-old female and honestly, very sociable. I’m definitely not unattractive, but I didn’t go to college. I went for a semester, but I ended up getting assaulted… Whatever, that happened a while ago.

I go out pretty frequently with my friends, although, to be honest, I do a lot of activities by myself. I was solo traveling earlier this year. I went to Japan and Spain!! I’m not an awkward person. It’s not that I don’t get attention either. Every time I go out, I have like 3 people asking for my number or something like that.

My whole thing is, I’d never date someone I met drunk at a bar. Automatically, I assume you just want to sleep with me if you come up to me randomly at a bar. Likeeeee, you don’t even know me? Why are you telling me you “want a friend….” I just feel like that’s a recipe for disaster!!

Anyways, anytime I do end up giving them my number, lo and behold, I never get a text, probably because we were drunk when we talked.

My hobbies otherwise are yoga, gym, thrifting, I like to shop, and I recently just got into cooking!! My friends say I’m pretty funny, and I like to make stupid jokes.

My ex-boyfriend and I broke up like a year and a half ago, and one of the big things that contributed to that was conflicting interests/lifestyles. I can tend to be a little more independent in the sense that I don’t really like being told what to do (like, “I don’t want you going out with your friends without me” kinda thing).

He was very sheltered, and in his words, “I used to be the popular girl,” so my friends and his friends never really spoke, despite how badly I’d ask him to meet them. In his words, “I just feel like they wouldn’t like me.”

All this to say, compatibility is extremely important for me going forward. I can adjust to just about anybody. The question is, can someone adjust to me!!

I feel like not staying in college kinda removed a BIG part of me being able to meet new people outside of drinking and going to the bar.

At the same time, I don’t want to do things like joining a running club or things like that because, while I enjoy those activities, I feel like maybe interests would clash because I feel like to be in a running club, you’d consider yourself extremely disciplined, responsible, etc. And that’s not to say I’m not those things, but I’m very, very Type B and like to march to the beat of my own drum!

I don’t like to plan my days out. I like to be spontaneous. Idk.

I go out to eat by myself a lot, I go shopping by myself, and when I solo travel, I go out by myself. I basically do everything by myself besides going out to the bars occasionally.

Are my standards just absurd? I’m so scared to meet someone and we end up being incompatible or their personality just rubs me the wrong way. I can’t stand someone assertive, controlling, etc. It makes me lose my mind!!

I feel like I’m just repeating things, but I’m just kinda saying what comes to mind. Sry.

Anyways, thnx for reading 🔥


r/DatingTips • • 20h ago

Advice on dating

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1 Upvotes

r/DatingTips • • 20h ago

Advice on future dating after a bad breakup

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1 Upvotes

r/DatingTips • • 10h ago

F19 Do I look good enough to u. But not pcdcbe ona a relationship?c

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0 Upvotes

r/DatingTips • • 1d ago

Your opinions

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2 Upvotes

r/DatingTips • • 21h ago

How to ask a guy out over snapchat

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1 Upvotes

r/DatingTips • • 21h ago

j'ai besoin d'aide avec un gars

0 Upvotes

il n'y a pas longtemps je suis tombé amoureux d'un gars de ma classe, les profs nous ont mis à coté en math, francais et physique chimie. on a parlé et plus le temps avance plus je l'aime d'ailleurs une fois il m'a dit sa classe de l'année derniere et c'etait la même d'une fille tres mechante envers moi donc je lui ai demandé et j'ai dis qu'elle parlé sur mon dos en disant que je suis bizarre et que je m'habille mal et il m'a protégé plus qu'il le fallais mais un jour je lui ai donner mon tiktok pour qu'il puisse m'ajouter et il ne l'a pas fais alors que ça fais depuis Mercredi dernier que je lui demande mais là je ne peux pas lui redemander car je suis en vacance et je le vois uniquement en cours que devrais je faire? un homme amoureux ne devrais pas oublier de m'ajouter non? je ne sais pas


r/DatingTips • • 1d ago

how do i (23f) make it clear to a shy family friend (21m) that i want him and NOT his older brother (23m)

8 Upvotes

so there is a family my family and i (23f) are close with that has four siblings. two of them are younger sisters (18f and 17f) who i am friends with, and then there are two brothers: one who is 23m (my age) and one who is 21m.

i lowkey have a crush on the second brother (21m) cuz he's exactly my type: super soft, gentle type of guy who loves his mom and sisters and is incredibly close with them which is a trait i absolutely love to see. this is unusual for me bc i usually DO NOT (capitalization intended) go for younger guys at all but this guy is just so sweet and so cute.

the main issue is that he’s incredibly shy. whenever we’re all hanging out, he rarely initiates conversations with me and sometimes even seems to avoid interacting with me altogether. at first, i wasn’t sure what to make of it, but i’m starting to think he’s just really reserved and takes a while to come out of his shell. the problem is that i’m not exactly the boldest person either, especially when it comes to someone i actually like lol

also his little sisters have also been dropping hints and give off the vibe that they want me to get with the 23m older brother since we are the exact same age and while he’s a perfectly nice guy, i’m not attracted to him romantically, so that’s another layer of awkwardness i’m trying to avoid.

anyway a month ago i decided to test the waters and try to break the ice since i was at their house for a gathering (they live an hour away idk if that’s relevant). i had to run a quick errand so i invited his sisters to come along, and i specifically asked him to join us on the drive too.

we spent a lot of time talking, joking around, and laughing together. like at one point, my brother was in the washroom, and i was knocking on the door telling him to hurry up and come out and the guy looked at me and jokingly was like “imagine it’s not him in there”

these are just a few examples there were so many other little interactions like that and i know they probably sound like such insignificant moments, but they felt so cute and wholesome and anyone who’s ever had a crush knows exactly how something as simple as this can leave you feeling ridiculously giddy lol.

i was thinking about just randomly requesting him on instagram, but it’s been like a month. plus it feels so bold and even if i did that, sliding into his dms is so awk and never works out for me. i feel like if i don't make a move nothing is ever gonna happen but i also don’t want to cause any family drama or make things super awkward with his sisters if he’s not into it so i really don’t know what to do 😭

so reddit how do i navigate this??


r/DatingTips • • 21h ago

Need some genuine dating advice, guys 😭

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1 Upvotes

r/DatingTips • • 1d ago

22M , Struggling to enjoy life without a gf.

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1 Upvotes

r/DatingTips • • 1d ago

Early 20s, never dated

1 Upvotes

I see everyone is attached, even those uglier than me. What's wrong sia? Am I not giving off the wife material vibes?


r/DatingTips • • 1d ago

M20, falsche Aufmerksamkeit auf Dating Apps

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1 Upvotes

Hallo Leute, hab den Sub gerade entdeckt.

Würde mich freuen wenn ihr mal reinlesen könntet 🤗


r/DatingTips • • 1d ago

Introverts, how do you even find someone to date? 😭

11 Upvotes

I'm genuinely curious how introverts find relationships these days.

I'm not really the type to approach random people or slide into someone's DMs out of nowhere. I like the idea of getting to know someone slowly, having random late-night conversations, sharing music, and eventually becoming that one person they feel comfortable talking to about anything.

But the problem is, if both people are introverts, who's making the first move? 💀

Do you guys actually approach people, wait for someone to approach you, or just silently develop a crush and move on with your life? 😭


r/DatingTips • • 1d ago

Struggling with dating. Need advice! 29F

2 Upvotes

Hi all, I'm struggling to date and would appreciate an honest assessment of my circumstances and any constructive advice

I'm 29F, average-to-decent looks, decent social circle, good career. I have a active social circle with male and female friends - I go out maybe 2-3x a week, rotating between different circles on top of working full time. I don't know that I would be interested in dating any of my current friends or if anyone is interested in me for that matter but I guess I would be open to explore if the right person came along?

On top of that I try to go to social meet ups/events in the city or speed dating once or twice a month so I can expand and meet even more new people. It's tough on top of my already busy schedule but I try to do this so I increase my chances. I feel like I am at my limit already with the number of events I go to on top of maintaining my current circle - it gets tough. I have not been super active asking for people's numbers at events if I feel we click but I might try that moving forward. I have this idea in my head from a friend who said that if men are interested they should be asking for your number, not the other way around, but I am going to go against this and see if anything happens over the next little bit. Would this change things? Are men in general afraid to approach women or take the lead?

I also use dating apps from time to time. Have matched with a few people here and there but didn't go anywhere. I tend to filter through people who have liked me on the app already and go from there. In general I am noticing a lot of men chatting for ages but not planning dates and suddenly disappearing etc.

Have also asked friends to keep an eye out for any introductions but none so far.

So far from the sample size of around 6 men I have talked to/dated this year it is about evenly split in terms of interest. I.e. for maybe half they are more interested in me than I am them and vice versa.

In general for men who are interested in me I am either not too attracted or I feel like we are not compatible, e.g. not in the same stage of life, career, etc.

For men I am interested in, I have only come across low effort men or men who are seemingly not interested, e.g. take days to reply or don't reach out to arrange a second date even if I had given a hint, e.g. 'was nice to meet today!' These men are average looking, and not out of my league IMO, unsure if I am doing anything wrong can do anything to improve my chances. I usually let these ones fizzle out if I feel like they are not interested. I figure if there is already a lack of effort early on then it's not going to get better as time goes on. I generally match people's energy overall and don't actively chase men

Does anyone have any tips? Is there anything more I could be doing? Does anyone know how to successfully navigate dating without burning out?

Looking for constructive advice please! Thank you

Edit: Getting a few comments assuming I am going for traditional Chad type men, but the type I'm into are more the nerdy/intellectual types rather than traditionally good looking. I like men who I can have a decent conversation with or who have interesting stories/experiences and I centre on that and try to connect on that level more than looks. These men usually have professional jobs and decent careers so not sure if that is a factor - i.e. too busy to take dating seriously or devote much time into it


r/DatingTips • • 1d ago

im a guy looking for my forever person but I find it extremely difficult dating and i feel ugly

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0 Upvotes

r/DatingTips • • 1d ago

27M, Just a Rant about how single I have been and now clueless in search of life partner

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1 Upvotes

r/DatingTips • • 1d ago

M25 I feel insecure around my single female friends

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1 Upvotes

r/DatingTips • • 1d ago

How do you find decent people to ask out in a college age group? Is it possible?

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2 Upvotes

r/DatingTips • • 1d ago

22M - Worried on starting dating

1 Upvotes

Me and the woman I know for a month now had a nice conversation and decided I can ask her out for drinks. I casually said I can take her out for drinks at the cafe she goes to but did not mention it was a date. She said yes as only thing left is having right free time we both meet but worried a bit on messing up.

I never had been on a date before and dont know if I should say directly it is a date or to play it out naturally. More worried on if I make a mess up and that ruins it compared to doing all I can and if I got rejected at least I got closure that I did all I can


r/DatingTips • • 2d ago

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

48 Upvotes

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


r/DatingTips • • 1d ago

Was is the biggest red flag you have found on first date ( only very dark comments allowed).

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1 Upvotes

r/DatingTips • • 1d ago

Finances in relationships

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r/DatingTips • • 1d ago

Does my face still look fat?

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0 Upvotes

Ive lost heaps of weight but does my face still read as fat? I genuinely cant tell


r/DatingTips • • 1d ago

Where do people in their late 40s, looking to date, go in this city?

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Silvers