Question about dating at age 27 as a guy?

[Anonymous]

Okay, so as it says in the title, I'm 27 (about to be 28 in May). As of right now, there are some things that I need to work on as far as improving myself before entering the dating scene. My question is, when im ready to finally get out there, how do I pick the right person if any? I never been on a date before, never been intimate with a woman, and I've been alone for so long that I'm used to it. Also, do you date foe the purpose to get married? The reason I ask is because I don't want to get married or have kids. I'm also not good with inherenting other people's issues. There's a lot I don't understand about relationships too. I look at the pros and cons, and usually the cons win. I don't know how to deal with other people's when they're sad, or mad, I fear if I do get in a relationship, I might get cheated on, I also fear rejection, which is another reason why I don't make the first move.

I've been single basically my whole life, so basically if I'm starting out now, most of the people my age are experienced. I'm all over the place with this post. This is the first time I voiced any of this with anyone, so that's why there was a lot to say.

[ZamerZ]

First question of mine would be why you even want to start dating now? Has it merely not worked out in the past, do you want a partner and a relationship bc of the same reason we all do (human connection, bonding, sharing a life etc.) or bc you feel societal pressure to do so? The pros and cons list sounds to me as if you're not sure yourself, tbh. Making a pros and cons list in general doesn't seem very convincing that you really want a relationship, especially bc the cons win - and you are entirely in control of the outcome of that list by the way, but feel free to clarify.

I used to be like that and I still love the status of being single because of all the freedom that comes with it. But as others already said, you have to be aware that people like you and me have it a tad bit harder in the dating pool because every potential partner will have to compete with our comfort zones and habits. Being single for a long time is great because you learn to love yourself as a person and to enjoy life on your own, but it also comes with that downside. We're used to our me-time and way we live our lives and making compromises on that and what we value can be a tough thing to agree on.

It's important that you're not looking for someone who will fit into your life bc we all are unique puzzle pieces who aren't meant to complete someone elses jigsaw of life. To pick the right person is a long journey and sometimes you're lucky, sometimes you're not. It's important to enjoy your time together but also apart and live your separate lives as healthy as possible as a couple. In my experience, the right person is like your best friend - you trust them, they make you laugh, you can be your authentic self with them and you go through thick and thin together - best friends, just with the benefits of romantic feelings and more intimate stuff, if that's what both are into.

Good communication is key if you enter the dating game. You don't want a marriage and a family? Great, just let any potential partners know from the beginning. Set boundaries. You can only get good at dealing with people and their emotions if you actually get involved. Sad, mad, happy and whatnot, you will need to learn to handle that all by yourself and firsthand experience. If you can't be bothered to do that part, don't start a relationship with someone. We all are afraid to get rejected, cheated on and all the bad things in the book. I can't tell you anything else but that you will just have to trust the other person and your own gut - learning how to read red flags, being attentive, getting to know the other one as good as you can so you know what's going on in the worst case.

Sorry for the essay, but as someone else here said - it's trial and error. Fuck around and find out - not literally, unless that's what you want - but the only way to learn about dating is, in fact, to date. No other way around it.

[ZamerZ]

*forgot to mention - a real game changer for me on the perspective of dating was Daniel Sloss's Comedy Special called "Jigsaw". Maybe have a look at the last half hour if the humour isn't your cup of tea, but he offers a bunch of really important points regarding dating and your life choices nowadays. He successfully broke up thousands of couples and marriages with that show bc they finally started to ask themselves the important questions that mattered. It's worth a look.

[Asker]

It's not scared of getting rejected. It's more of I assume that they'll say no, so I never ask.

[SueShe]

There is no age to start dating. However, the longer you wait, the more difficult it becomes because you have made your nest and have your habits that will be difficult to change. The biggest challenge will be to integrate a person into your life and daily routine.

Now, your fears are justified unfortunately because our modern society does place an immense importance on trivial stuff like sex, looks and less about the character and personality.

If you don't provide and expectations are not met, then yes, you will be cheated on. It is very sad to say that sex is the predominant factor in a relationship and it applies to both genders.

[Oliverlogan263]

Hey man, don't stress too much - being a late bloomer in dating isn't such a bad thing nowadays. Listen, first thing is you gotta get comfortable just being around women as friends, so join some social clubs or intramural sports where you can hang out without pressure.

When it comes to dating, don't go in thinking every girl has to be "the one." Just see it as practice getting comfortable talking one on one over coffee or whatever. Make sure she knows you're still learning dating ropes so expectations are clear.

As for trusting issues, take it slow and pay attention to how she treats not just you, but others too - does she respect boundaries, listen actively, keep promises? A good person will earn your trust over time.

And don't compare yourself to dudes who dated forever - focus on growing your own experience level without judgment. Your special lady is out there, man, but she'll come along naturally as you practice feeling comfortable in your own skin first. Stay positive!

[Cheapskate]

How to pick the right person? It's trial and error, but you should go for someone you are attracted to and then take it a bit slow and figure out over time if that is someone you would want to be with long term. And be honest about what you want and don't want so that you can find someone compatible. Communication is good.

The best possible resource I can recommend (and it is still very imperfect), is this defunct website called The Mating Grounds. I uploaded a PDF of some of the key advice:
https://jmp.sh/s/jjBfZc7MmLIco1eGYfhn

They also had a podcast of the same name, which is still available.

But the best teacher is personal experience. The more times you try, the more you will learn.

And don't worry about inexperience. It's not that important.

Also, don't rush into sex. Be careful there. Sex is fun, but it can really get you into trouble, so choose carefully who to have it with, and protect yourself from STDs and unwanted pregnancies when you do.

[Cheapskate]

Podcast:
https://podbay.fm/p/the-mating-grounds-podcast

Also, this is a really great explanation of how love works, and might help you avoid some pitfalls:
https://helenfisher.com/about/

[Anonymous]

I didn’t meet my future husband until I was 29, and one thing I strongly encourage when it comes to finding the right person is to lay all the cards down from the very beginning. What I mean by this is, let your desires, views, and opinions regarding certain topics be known from the beginning.
If you don’t want marriage, let it be known right away. If you don’t want kids, let it be known right away. It’ll save you and the other person from wasting time.

[Anonymous]

You need therapy. Being this insecure is crippling.

[Anonymous]

Another reminder oh well