If you’re joining the wonderful world of dating for the first time, whether online or in real life, perhaps after divorce or a break-up, you may find things are not quite as you’d expected. I want you to have healthy, enjoyable dating experiences, so here are some top tips and lessons others have learnt the hard way!

Fantasy date

If you’re trying online dating, you can very easily build up a fantasy person from online chatting which bears very little resemblance to the actual person! It’s impossible to guess what someone who is three-dimensional and moves around is like from a static picture. Whether we meet in real life or online, we all project our own wishes and needs onto the other person. With online dating, we may fill in the gaps in their messages or even make up a voice for them as we read. Research has shown that people are often disappointed by their dates when they meet in real life.[1] Don’t message too much and meet them after just a few days; and be on your guard not to reveal too much during that time. Phoning and video-calling first can help.

We filter out the warning signs

At first, you may be so relieved to meet someone you can talk to and let your guard down with that for a while you ignore things that aren’t right about the person. As you date more people, you’ll learn to notice these and become more picky early on. Read back over the messages AFTER things don’t work out and you’ll soon spot the signs.

The illusion of connection

You’ll probably experience the intoxicating illusion of a quick “strong connection” with someone. It happens more often that you’d think and it’s not the basis for a relationship. The connection is with a fantasy, not a real complex person. It represents our need for warm connections with others. You’ll soon realise that there are other considerations, like shared values, emotional responsiveness, empathy, listening skills, and how they deal with difficulties that are needed to keep the connection going. Don’t let the emotional power of the connection cause you to put up with mediocrity or being treated badly!


Photo by Matheus Ferrero on Unsplash


Dating can often involve a lot of attention, hundreds of messages, quite intense emotions and a lot of sharing of personal stuff at the beginning. This can often wear off quite quickly, especially after sexual intimacy, and you or the other person may withdraw. If they withdraw before you, it can be easy to become insecure and start wondering what you did wrong, but this is just a very common phenomenon in today’s dating game. After dating a few different people, you’ll find it happens to you too. It often means the person didn’t turn out to be the perfect partner you thought they would be. It can also be because you’re protecting yourself against rejection, getting hurt or the fear of not being in control of your emotions. You’ll learn to be more sceptical at the beginning and not get so swept up in the hopeful euphoria of thinking you’ve finally met the person of your dreams!

Expect short-term experiences

When you first start dating, it’s best not start looking for a serious relationship. Accept that you’re most likely to have a series of one-off dates and short-term relationships while you’re adjusting to the norms of dating and working out what your needs are and what kind of person you’re looking for. If you take this approach, you will protect yourself a little from getting hurt. Once you get the hang of it, you can become more focused on looking for something serious.

Dating more than one person

If you can, don’t just arrange a first date with one person: arrange several. It’s a great way to stop yourself getting involved too quickly, good for your self-esteem, and it makes you less likely to put up with stuff. It’s like buying a house or a sofa:  you need to try out a few to compare before you know what you want.

Dating several people is the norm for online dating, so don’t assume your date is only dating you, although this is not usually explicitly revealed! Exclusivity is usually discussed a few dates in, possibly before getting intimate, but not always.


You may have generic emotions that can easily and quickly become associated with a particular person, even if they’re not right for you. They are probably partly grief for previous relationships, partly a need to feel loved and understood, partly an expression of the depth and complexity of the human experience. If you date more than one person at a time you’ll see that it’s quite easy to have the feelings for more than one person, meaning that it’s not really about the other person,but about the fundamental need for warm connections. You’ll learn to relax and enjoy your feelings while remaining essentially self-sufficient. Remember they are just chemicals swirling around in the brain and get your need for connection from cuddling a teddy bear or a pet as well, so you’re not dependent on one person!


You will probably find when your first dating experience/short-term relationship comes to its inevitable end that you’ll suffer quite a lot. If you’ve had previous relationships, it may bring back many of the feelings you had when you split up from your long-term partner, and it can feel even more painful than that. Treat it as part of the grieving process. It’s like when a new bereavement can bring back the pain of a previous bereavement – it is a necessary stage that we have to go through. When you’ve experienced a few endings, it’ll become easier. Endings are inevitable in all areas of life. Be kind to yourself.

When ending a dating experience or relationship, many people say something like “I’m not looking for a serious relationship”. This is often code for “I don’t think you’re someone I want to get serious with”. If you want to end it, do it gently and kindly. You’ll learn to treat each other like a mutual interview, rather than feeling like you’re the one on trial and not getting the job. Just because you’re not right for someone, it doesn’t mean you should value yourself less. Often, we know deep down the other person isn’t exactly right for us but we wait for them to end it. You just need to keep on looking and enjoy the process!


Photo by Kinga Cichewicz on Unsplash

Supporting yourself through online dating

OK, so you are probably too scared to do any dating at all after all that … But it will be fun, too, I promise!

It can make a big difference if you have some support, to ask questions like

  • Which dating apps should I use?
  • How many messages should we send before I suggest we meet up?
  • Should I kiss on a first date?
  • How do I know they’re interested?
  • How long should I wait before having sex?
  • What red flags should I look out for?
  • How do I flirt?

Knowing some of the stats – such as demographics on dating apps, or how many messages lead to dates – can help too. And it starts with knowing what you have to offer a relationship and feeling good about  yourself. So do get in touch if you’d like support or advice in getting started with your dating.

You can book your first session here and buy my workbook here.

You can also sign up for my group coaching programme here.

You can watch Rachel give some more tips here:

[1] Frost, J., Norton, M. I., & Ariely, D. (2007). Improving online dating with Virtual Dates. Proceedings of the Association for Information Science and Technology, 44(1), 1-15.