How To Get Back Into Dating | The Ultimate Guide (Updated 2022)

How To Get Back Into Dating | The Ultimate Guide (Updated 2022)

Written by dating coach for men Gary Gunn - Founder of Social Attraction

In this article, I will give you my ultimate guide on how to get back into dating. I will outline the top 15 ways that you can use immediately that will help you start dating again.

Included are diverse dating ideas to:

  • Develop your dating confidence (at a comfortable pace)
  • Help you rethink your dating strategy (creatively)
  • Meet and attract women (by different means)

In the final section, you will find some FAQs that will prove invaluable to anyone who has not dated in a while.

If you want to get back into dating with immediate results, then look at our client testimonials and book onto our next confidence course. Watch them on YouTube here: Confidence course for men reviews:

dating confidence course for men

Set a dating goal

What do I mean by setting a dating goal? I mean taking a pen and paper and writing out exactly what you want from your life. There are multiple reasons why this is good for you:

  • It stops you from focusing on your past
  • Helps you let go of previous events
  • It serves to illuminate your future

You can then focus on the types of women – or the specific woman – that you would like to meet, attract, and date in your life. The more specific you can be with your dating goal, the easier it will be to implement some of the other lessons from this article. It will ensure that you frame any new relationship the right way from the start.

My infographic below outlines three invaluable ways to help you do this. Read my healthy boundaries with women article, which goes into each of these ways in more detail.

3 ways to embed healthy boundaries in your dating life

Online dating

First and foremost, I have recorded a few podcast episodes on the best online dating photos to use for anyone who wants some guidance on what pictures to use for their online dating profile. You can also refer to my infographic directly below, which gives some immediate help in taking effective online photographs.

With online dating, you must put a few boundaries into place to make it easier for you. The most important boundary is to limit your time. I recommend only online dating for an hour a day. If you give any more time to it, you run the risk of it taking over your life.

Limit your time dating

An example of a firm boundary is:

“Between 7:00 PM to 8:00 PM I’m going to online date. I’ll reply to as many messages and send as many as I want to in that hour. But after that, I will log off and I won’t look again until tomorrow.”

Also, remember you do not have to download the dating app or else your phone will be permanently beeping. This is both irritating and inconvenient. You will find that having a set boundary or time limit with online dating will achieve the following:

  • A healthier mental well-being
  • You will not be so readily available
  • Women will wonder why you are not replying

This will help build mystery and attraction with the women you are messaging. For further detail on the infographic’s advice below, read my best online dating photos article.

A guide to attaining 3 ideal online dating photos

Speed dating

All you have to do is log online and type in speed dating, including the area where you live, then book yourself on to one event a week. It is that simple. There is a method of going weekly to a speed dating event:

  • It allows you to get dressed up
  • It puts something in your calendar
  • You never know who you will meet

Another bonus is that it is a perfect opportunity to meet other guys who are single. Guys who perhaps will know more about getting back into dating. There may also be other single events that you can go to together to meet women.

So speed dating is a great way of meeting women and meeting a potential new friendship group.

Take a confidence course

Another important aspect of developing confidence in your life is to find people who are further down the line than you. Find role models who are single and who are active in their dating life. Find out what they are doing and how they are doing it. This will inspire you to go out and take control of your own dating life.

My company, Social Attraction, runs confidence courses for men. These courses are designed to help you overcome your fear of approaching and become better at communicating and flirting with women.

We host a range of different courses covering digital products, classroom-based teaching,  1-1 Skype coaching and taking you out into the real world to help build your confidence with women. To learn more about our coaching, visit our confidence courses page and book a consultation call.

If you want to learn more about how to approach women in the day – otherwise known as daygame – then see my infographic below. You can also read my related daygame article where I go into various aspects of daygame, including different strategies and how to attain the success mindset.

3 main points depicting Daygame

Reconnect with old flames

It may have been through work or friendship groups that you met a previous partner. Time has passed and perhaps they are also now single. Interestingly, this could prove to be a decisive aspect of your life.

Perhaps you broke up with someone amicably years ago because their career was going in a different direction to yours, but now you are both single. You are looking at getting back into dating – and they could be a perfect match for you at this stage of your life.

Use social media

It is easy to get back into contact with people with social media. All you have to do is look online, send a friend request or follow someone. You will be able to establish whether they are single or in a relationship very quickly.

If they are single and you both ended the relationship on good terms, why not try reconnecting with them. Perhaps organise to meet up for a coffee or a drink. In principle, reconnecting with old flames can be an excellent way to aid your confidence when getting back into dating.

For anyone wanting to get back together with their previous partner, you will find a helpful infographic underneath that outlines ways to help you get your ex-girlfriend back. I also suggest you read my how to get your ex-girlfriend back article.

How to get back into dating by getting your ex girlfriend back

Meet women in your day-to-day life

If you take a moment to consider just today –  how many attractive women have you seen that you would have approached and engaged in conversation? That is if you had the confidence…

Being able to approach and speak to women you encounter as you go about your daily activities is transformative. It would instantly give you more confidence and offer a bigger dating pool of women to attract and date. However, this all begins with having the confidence to go and talk to a woman.

I have written several articles on overcoming the fear of approaching women, which is a huge sticking point for many men that I coach. One of which is my beat the fear of approaching women article that you may find helpful. You can also take a look at my related infographic here:

3 suggestions to overcome approach anxiety in meeting new women

Take a singles holiday

Very simply, you log online, type in singles holidays and find somewhere in the world that you have always wanted to visit. Then book onto a singles holiday then and there. In doing this, you are cementing something in your diary where you get to go on holiday with the potential of meeting other people.

Furthermore, while you are there, you can think about what it is that you want from your dating life. It will provide you with a different perspective from the monotony of day-to-day living and you will also have a valuable respite from life and work

Multiple companies offer single holidays and where you can check their reviews. So just go online and book one.

Go on a bar crawl

Going on a bar crawl may sound a bit left field. However, bar crawls are great because travellers from all over the world tend to go on bar crawls in the city they find themselves in. Often these people travel by themselves, so you will find they are usually receptive to engaging in conversation and spending time together.

Additionally, when on a bar crawl, you are together for a set period of time. This means there will be multiple opportunities to interact with the women there and get to know the guys there. This offers another great way of getting back into dating.

Added bonuses:

  • You get dressed up
  • Everyone has the same sociable vibe
  • You meet people from all over the world

Recognise signs of flirting

To recognise when a girl is flirting with you – whether it is on a bar crawl or any other scenario – take a look at my handy infographic underneath.

I also suggest you read my signs she wants you sexually article to make sure you don’t miss out on recognising any go-ahead signals from a girl.

5 signals to look out for when a woman is attracted to you

Stay in a hostel on holiday

If this had been suggested to me ten years ago, I would have replied: “You’re being ridiculous. I don’t want to stay at a hostel. I’ll stay in a hotel. It’s much, much nicer.”

The benefit of staying in a hostel when travelling solo is that you are by yourself, but, importantly, so are all of the other travellers. This is a valuable opportunity to connect with new people from different cultures and walks of life. Another bonus is that hostels know what is going on in the city you are staying in. So all of a sudden you are in a new city…

  • You are meeting people at your hostel
  • There are events that will be put on for you
  • You meet a different type of woman from another culture

This allows you to get back into dating in an easy and fun way.

Conversational confidence

Underneath is my infographic that will help you effectively speak to new women. It shows you the three types of intelligence to convey in conversation to make a positive and lasting impression.

You can read my how to carry on a conversation with women feature to learn how to implement these effectively.

3 types of intelligence to convey in your conversations with women

Join a new gym

You may already train at the gym. However, changing to a different gym gives you a new experience. You are now single. You are now actively dating, so you can become more sociable when you join a new gym. And you can talk to more people; in essence, become a new person.

Changing your gym is a worthwhile way of energising yourself and kick-starting your confidence.

If you are not training at all, this is also an excellent way to build your confidence and assist you in feeling better about dating women.

Join a social club

It is worth remembering that the attractive man who leads an attractive lifestyle spends his time doing activities he enjoys. Additionally, you can also talk about your new interests when you speak to women. It can be a book reading club, it can be a salsa dance lesson, or it can be a sculpting class, for example. It does not matter what it is as long as it interests you.

By booking onto a social club, you are likely to meet other people with similar hobbies. Perhaps they are single themselves and it can lead to a potential relationship. Or perhaps they will have friends and they can say to you: “Oh, you should meet my friend. She’s also single…”

Hence doing something that you love in your spare time is another way of getting back into the dating game.

How to speak to women

Below, my infographic teaches you how to flirt with women in any social setting. These five principles are fun to apply when you have met a girl and want to make a confident, memorable impression.

I also suggest you read my corresponding how to speak to women article, outlining how to implement each technique into your conversations.

5 conversational techniques that will make her remember you

Find a confident wingman

There are multiple ways of finding wingmen, such as going on nights out, bar crawls or social events. The aim is to find someone who is:

  • Social intelligent
  • Socially aware and willing to go out
  • Actively single and wants to meet more women

Spending time with someone like this will allow you to learn from that person as a role model. You will also get more dates in your diary where you are going out and actively meeting new people.

To learn more about ‘the attractive man’ qualities, look at my infographic underneath. In my related dating tips for men feature, I talk about each of these nine qualities and how they make you more attractive to women.

9 psychological techniques that attractive men use around women

Seek out modern dating advice

I recommend reading blogs and books with modern dating advice and listening to dating podcasts like my one – The Gary Gunn Show. In principle, you want to gain a better understanding of the modern dating world:

  • Where do single people go?
  • What are the mechanics of dating nowadays?
  • What common pitfalls and mistakes do people make when trying to get back into dating?

By reading books and blogs, listening to podcasts and watching videos, you start to bring your dating goals to life. This is because you become more aware of what is socially acceptable in the current dating scene.

Below you will find an infographic that offers my top five dating lessons for life. This will help you immeasurably in your dating interactions. Read my corresponding dating lessons for life article here for more detail on implementing these lessons.

5 principles that enhance your dating interactions with women

Ask friends if they know any single women

Meeting new women through people you know is an effective dating method because there is already trust. There is already a connection through your mutual friend. And your friend is more than likely going to be able to give you a warm and glowing introduction.

When we have a warm and positive introduction to a girl, it is much easier to organise a date because the trust has already been established. This means you can focus on getting to know her in conversation.

Also, you already have a commonality with your mutual friend as a subject of discussion. Therefore take the time to ask your friends if they know any single women you may be compatible with.

Effective flirting

I have included my infographic below, which offers three techniques to follow to amp up on your conversations with a woman on a date.

You can also read my complete how to flirt with women article in full where I give another 17 additional ways.

3 seduction techniques to use with women

Become a local dog walker

There are many apps nowadays for anyone who likes dogs, where you can register to be a dog walker in your spare time. Guess what happens when you take dogs out for walks? Everyone wants to come and talk to you!

Registering as a dog walker does the following:

  • It is an active hobby
  • You will be out and about more
  • People (including women) will approach you

This is an excellent way to get back into dating because it is a low-level investment and it is fun. You are simply walking a dog and allowing other people to initiate contact with you.


How do I date after years of being single?

For anyone who has been single for years, it is difficult to have the confidence to get back into dating. In this article, I have given you a step-by-step methodology that you can follow. Above all, I advise you to take it slowly. Start by taking out a pen and paper and writing out what you would like from your dating life.

The smaller you make that initial investment, the more likely you will follow through on it. Once you have done that, it is then“Okay, what’s next? What can I now work on?”

When you take that next step, your self-efficacy begins to grow. Your confidence will also be raised when you take it one step at a time. This allows you to get back into the dating scene in terms that are comfortable to you.

How long after a relationship should you start dating again?

The timeframe on how long you should wait before you start dating again is different for everyone. If you have accepted and healthily processed your break-up, then you could start dating as soon as possible; what are you waiting for?

You want to be going out and meeting new people. You want to actively have a better social and dating life sooner rather than later. I am not stating that the new women you meet will be long-term relationships from the start. Instead, I am saying that there is no value in staying single if you want to get back into the dating game.

For anyone who does not feel ready to start dating and wants help in processing that period of their life, I recommend doing a meditation practice. Having the ability to clear negative emotions will help regain your emotional control and create a healthy mindset.

My infographic below also gives further helpful advice to any man looking to date after a divorce. You can read the entire dating after divorce for a man article to learn more.

Seven ways to get back into dating after a divorce for a man

How do I start dating?

This one is simple and it is fun – start dating. You just need to switch your attention. Focus on what you want from your dating life and what women you would like to meet. Once you have worked that out, then comes the fun aspect. Go out and start dating different types of women. Enjoy different types of conversations.

You can then start deciding who is the type of person you would like to attract into your life and the type of woman you would like to date long-term.


  • Set a dating goal
  • Online dating
  • Speed dating
  • Take a confidence course
  • Reconnect with old flames
  • Meet women during your day-to-day life
  • Take a singles holiday
  • Go on a bar crawl
  • Stay in a hostel on holiday
  • Join a new gym
  • Join a new social club – doing something that you love
  • Find a wingman who is already confident with women
  • Seek out modern dating advice through blogs, books and podcasts
  • Ask friends if they know any single women
  • Become a local dog walker

Written by Gary Gunn

Gary Gunn is the bestselling author of An Education In (Online) Dating.

He has hosted over 1000 dating confidence courses in the UK and Europe, as well as over 1,500 courses conducted online.

Moreover, he is the head coach at Social Attraction and leads the team, training and courses.
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