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How to Get Back into Dating after Being Single for a Long Time as a Guy

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How to get back into dating after being single for a long time? When you had a breakup, and then stayed single for an extremely long time, it can be very difficult as a man to get back into the dating scene because, well, you’re out of practice. Honestly, women have it so much easier after a breakup, even if they decided to stay single, they essentially have to do nothing but I suppose, to not forget breathing. Some guy will hit on them within the very, very, very foreseeable future. But as a guy, you’re all on your own, and there’s nothing more true than the saying “You make your own luck” than for a man who wants to find a girlfriend after being single for a long time. It’s not easy to make your own luck, so, let’s talk about getting fortune in your favor when you feel insecure to date again.

Hey guys, welcome back to the Breakup Corner, I’m Andi Galster, and here I teach men how to move on from their ex-girlfriend. But, well, I guess in today’s post, it’s about the fact that you probably have finally moved on. And, well, let’s just assume that it took you a while. Maybe it’s been a year that you’ve been single. Maybe it’s been two years. And hey, let’s be real, the older we get, the more likely we are to stay single for a long time because we don’t just jump into any random relationship, so some of you may have been single for a bunch of years. Honestly, even myself, as a dating coach, have gone through some times of being single for a long time. I suppose partially due to my life circumstances. 

I could have dated many girls if I wanted to, but even I understand the difficulty of getting back to dating. Even if you are like me and technically women are super into you because you got extremely good flirting skills, still, getting into new relationships is always challenging after a long time, because you have to start to be more open-minded towards letting another woman into your life. You have to be more open towards what you accept from women, because when you’re single, you may be more critical of a woman’s behaviors, ideologies, etc… But well, if you want to date, then you have to feel inviting to women, obviously. 

Anyway, I digress. I assume for most of you, getting back to dating is mostly a matter of lack of confidence, or it just doesn’t feel right. You don’t know how to get started at all any longer. Maybe you can no longer relate to dating apps, or maybe you don’t think you have what it takes to approach women. Some of you may still have doubts about yourself because of the painful way that your relationship with your ex ended, and perhaps your ex-girlfriend rejected you in a very direct and hurtful way, and so now you have your guard up towards other women, and at the same time, your ex-girlfriend crushed your self-esteem back then. 

There are so many reasons why dating again after a breakup is tough, and the longer it’s been since you’ve dated, the harder it may feel to you to date another woman again, but I think it’s important to recognize that you are overcomplicating the entire experience of dating women. Let’s for a moment not talk about dating, and instead, talk about your as a man, or well, we don’t even have to make this about gender at all. 

Anybody can get back into dating at any point in time. Of course, a woman will have it easier because she essentially doesn’t have to work for male attention, but, let’s talk about the act of socializing for a moment. Dating is essentially nothing more than being social and adding an element of physical and romantic attraction to it. I assume that you have been going on with your life for the last months, or years without being a completely anti-social, isolated person. 

Actually, I live in Japan now, and here they have a phenomenon called Hikikomori, which are people who just disappear from society and barely leave their houses. I assume this is not who you are. You probably know how to go out to a networking event, or how to go to a runner’s club, or how to strike up a conversation with some people in a coffee shop, at a bar or club, and so on. 

If you have these skills, then you already know how to interact with people. What that tells me is that you, in general, don’t lack confidence to be social. The only thing that you’re afraid of is that women will reject you, especially because you don’t know how to get a woman turned on any longer. And sure, that can and will probably happen. But if right now, you are not a socially awkward penguin, then I guarantee you that you are already ready to date again, and whether it’s been one year, two years, 5 years, or 10 years, it doesn’t matter that it has been a long time since you’ve gone out on dates.

So the most important thing if you want to start dating again, is to ask yourself if you’d be ready for the following: If I were to ask you right now, “Hey, let’s go to this or this event next week,” will it make you feel anxious. Or would you be excited to go out and do something fun? Would you look forward to meeting new people? If the answer is yes, then you are ready to date women. And if the answer is no, then you have to work on becoming more social again in small ways, by going out to new places every now and then, so that you normalize being outgoing, doing small talk, and talk about random things that are fun.

Of course, you’re now going to say “but I don’t even know how to talk to a woman any longer,” and so you think your dates will suck. First of all, you can meet women when socializing. And often, you can practice flirting at the same time as well, if the woman is into you. But more importantly than that, yes, you are 100% right. Your first dates that you go on will feel weird. That’s OK, dude. Just consider your first five dates to be trial runs, have absolutely no expectations, and if you end up being positively surprised and you actually connected with the women that you went out with, then that is simply a bonus on top of you having gotten back to the first dates. 

All that’s needed to succeed on a date is positive energy. This is why I talked only about socializing so far. If you’ve ever been full of energy and had a lot of fun in a social setting, then you probably know how attractive you were to everybody in the room, and maybe women even approached you because of this as well. The mistake that a lot of men make when they haven’t been on dates for a long time, is that they project a lot of negative energy on women.

You BELIEVE that you have no charisma, and so you become awkward on the date. But if you would show up on a date in the same way that you’d show up in a normal situation when you’re going out with friends to some sort of event, then most women would immediately like you. Most women that you go out with have no idea what your background is, how insecure you feel, how long you’ve been single, how hard the breakup with your ex-girlfriend has been on you, and so on. 

And the truth is, most women don’t care and you don’t ever have to tell them, unless they ask for any of it on a date. And for the most part, they surely won’t ask you this stuff, except for maybe how long you’ve been single. And when a question like this comes up, you can just make something up about the reason why you’ve been single for a long time. Like you wanted to focus on yourself for a while. That’s it. Maybe that’s even partially true. Now, I don’t encourage you to straight up lie to the women you go out with. Obviously, try to find some reason that aligns with why you have been single for a long time, but make sure it paints you in a positive light. But to be honest, I don’t even think most women would ask you this on a first, or even second date, so don’t sweat it. 

The only thing that matters when you go on dates after long periods of singlehood is that you are full of energy. That you are excited to meet the girl that you’re on a date with, that you show interest in her. Curiosity is the key to a good relationship, and when you are curious about a woman, she will fall for you faster than you can imagine. Of course, chemistry and so on play a huge role, and if you lack confidence in general, then reading dating books is certainly a great idea, but in the end, the only thing that you need in order to succeed on dates with women, even if you’ve been single for half a decade or even longer, is good energy.

If you know how to have fun, enjoy your time with yourself and others, if you actively seek to live a good life, even as a single man, then any woman will want to join you to have a fun life together with you. So, don’t be so stressed about your first date. Instead, ask yourself if you’re currently having enough fun in your life? If not, then I would like to challenge you to try to have 3 times more fun in the next 2 months than you usually would have, and then, when you are at a high of feeling really good about life, that’s when I’d like you to go on your first dates.

I don’t care if you meet a woman on a dating app, go on blind dates, get introduced by a friend, or try to meet some women in public, for example. by going to volunteering opportunities. Just make sure you make it easy for you and a woman to go on a date as soon as possible, and show her your positive attitude directly on the date. So that means, for example on dating apps, don’t even worry about being charming, etc… Get to the point quickly and try to get her to go out with you after no longer than three days of talking on the app, and to be honest, you can quite frankly try to get her to go out with you as quickly as possible.

The goal is to have face to face dates and replicate the positive energy of your normal socializing behavior on a first date. So, don’t be afraid to date if you’ve been single for too long. If you don’t feel like you are a ball of positive energy right now, then first follow my 2-months challenge of consciously choosing to do a lot of fun and social activities and then go out on a few dates. Maybe try to get your first dates rolling in a few weeks before the challenge ends. Don’t overthink it too much, you can do this!

Anyway, that’s all I’ve got for you this time.

How to Get Through your Breakup with Science

Hello there, I’m Andi Galster. I’m a dating coach and breakup coach for men — with a focus on dating science and dating statistics. I hope this inspired you, motivated you, and lifted your spirit up. I know you must be going through a lot. Don’t give up hope! You can get through this!

If you need even more help with processing your breakup, and finding new meaning in your life, then consider getting my book “No Contact Myth,” which is filled to the brim with advice on how men can move on from their ex-girlfriend with strength and confidence.

No Contact Myth | Progress, Not Pursuit | Why Men Must Move On And Not Chase Their Ex

by | Sep 25, 2025

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