Dating tips9 minutes

The Essential First 10 Dating Milestones In Your New Relationship

Laura, 26 November 2019
The Essential First 10 Dating Milestones In Your New Relationship

From those first butterflies when you see their photos on one of the best dating sites, the excitement of your first messages, arranging that tricky first date (when are we both free? what’s the best location? what should I wear?) and beyond, your dating journey is made up of a number of significant dating milestones. Here’s how to navigate the top 10 milestones in their usual order:

Dating Milestone 1 – First Date

Your first and second dates are absolutely crucial. Take a firm hold of your nerves and plan your date at a casual venue; a cute coffee shop or a quieter bar after work. Do what you need to do to get into a positive mindset before the date, especially if you have had a busy day: listen to your favourite songs, go for a run or hit the gym – whatever ritual works for you.

Keep the first date fun, light-hearted and fairly short. Show an interest in your date’s life, work and interests (without turning it into an interview). Don’t forget to share your own interests too and the things that are important to you.

When a date goes well, be proactive, let them know you had a great time (find out when to message after a first date) and would love to see them again. Enjoy that wonderful ‘I can’t stop smiling’ feeling as you walk away, feeling happy and excited about the prospect of a second date…

Dating Milestone 2 – The First Kiss

If you’ve got that special spark you might tick off milestone 1 and 2 on one date! One of you has to make the first move; turn on your ‘I’m going to kiss you/kiss me eyes’ so your date feels comfortable making the (first) move – learn how to build sexual attraction on a date.

If one of you is shy and prefers a kiss on the cheek as a ‘get to know you’ on the first date – make sure you do you best to set up that first kiss on the second date. After all, if you like someone, you don’t want them to have any doubts; you want them to know it!

Dating Milestone 3 – Do We Want The Same Thing?

As well as having fun dating & finding out what you have in common, if you are looking for a relationship it’s a good idea to check you are on the same page quite early on so as not to waste your, or their, time (& also prevent hurt feelings later on).

During date 2 or 3 have a chat about what you are both looking for, in a light hearted way. Listen to what they are saying. If you both want something different with no room for compromise, stop and look for someone else who shares your goals. If you both want a relationship, great. If things go well you could end up in the relationship you both seek.

Dating Milestone 4 – Doing The Deed: Sex!

One of the most common questions I get asked is “how many dates should you go on before you sleep with your date?” I recommend getting to know them well enough to see if you share common values and the dating/relationship goals first.

Another question I often get asked is whether to talk about exclusivity before you sleep together? Well, that depends if are you happy to sleep together first, then wait and see what happens, without assuming that dating will work out with that person.

Remember the basics when you invite your new date home with you – make sure your place is clean, tidy and inviting, have a playlist and perhaps a glass of wine or two to help you both relax. And obviously the exclusivity chat can happen after you’ve slept together, it’s whatever is right for each individual couple, it’s your communication and honesty with each other whatever stage of dating you are at, that is the most important thing.

Dating Milestone 5 – The “What Are We?” Chat

If it’s a relationship you want – unless a guy or girl acknowledges they are in a relationship with you – don’t assume it’s just you and them. Plan what you would like to say, and ideally have the conversation about your wish (all going well) for an exclusive relationship.

Real life examples:

Mike asked Jane (the girl he was dating) “How would you describe me to your friends?” She replied, “I’d say I was only seeing you.” Mike wanted to be upgraded from just a date to exclusive, and during that conversation he was.

Tanya was going on a theatre & dinner date with Rob. At dinner she mentioned to Rob that her brother had asked her what she was up to that evening. She’d replied “I’m going out for dinner with my boyfriend.” She stopped and looked at Rob “Is that okay, are you my boyfriend?” He said “Boyfriend is all right, that’s okay.” Tanya checked “So, you are happy to …” and Rob confirmed with a “Yes!”

Getting confirmation is is super important if you’re looking for something long term, so get the ‘so what are we?’ out of the way asap.

Dating Milestone 6 – Spending More ‘Free’ Time Together

When first dating, even if you are sleeping together, you might not always stay the night, and if you do, you may leave early the next morning. As you get to know each other, the weekend can be an excellent time to stay over, hang out and share the everyday things of life, which are all part of becoming a couple.

Dating Milestone 7 – Meeting the friends

Meeting the friends of the person you’re dating is a very good way to get to know someone. Spending a lot of time with those closest to your significant other can give you valuable insights into who they are and where they’ve come from. Once you start introducing your new partner to your friends, you are officially becoming an item.

Dating Milestone 8 – Say “I love you”

Saying “I love you” is a huge dating milestone which takes your relationship to another level. Once you say it – you can’t take it back! It could happen at any point – some people say it more easily than others, and is usually a true indication of how serious they are – although if they say ‘I love you’ straight away they may be less serious, so don’t be flippant.

It can be a good idea to wait till you are fairly sure they will say it back. The last thing you want is to say ‘I love you’ to someone, and have your declaration followed by an awkward silence…

If you aren’t ready to say it yet, but are keen, you could lead up to it with lesser but equally warm declarations of affection, i.e., ‘I adore you.’ ‘I love doing things with you.’ ‘I love certain things about you’. The ‘love’ word is bubbling around, but your declaration remains unsaid until the moment when you are ready.

Dating Milestone 9 – Meeting The Family

Wait until you are in a committed relationship – it’s not fair to put either you date or your parents in a situation where they get to know one another if your date is only going to be around for a few weeks.

When the time is right, don’t make a big deal out of it. Just invite them. Dave and Michelle who have been seeing each other since March have their own code. Whenever one of them brings up something a bit more serious i.e. that would move the relationship forward, they preface it with “I’ve had an idea, should we do …together?”

When you meet the parents, be as calm and relaxed as possible, if you are coming for dinner make sure you bring a bottle of wine or a small gift. Meeting siblings is very significant too when over 30, it can be as significant as meeting parents. Read our top tips for meeting the parents.

Dating Milestone 10 – I Becomes We, You’re ‘Officially A Couple’ And Everyone Knows It.

If all is going well months or a year into dating, if its now becoming regular to share your weekends, significant occasions, birthdays, holidays, Christmas, New Year, Easter and company functions as your +1, you’ve taken your relationship to a new level.

When you find yourself thinking about the person you’re dating first thing in the morning and last thing at night. When it becomes very natural for your thoughts to turn their way, and you can’t imagine life without them. When they are the first one to call you on your birthday or when they turn up to meet you after work on Friday and whisk you away for a weekend…you’ve made it through the initial dating milestones.

Remember there is no timetable for dating milestones. Some relationships move fast, others move slowly. Be fair to yourself and your date, try and take it slowly enough that you get to know each other properly and fast enough to ensure the relationship does progress through these stages of getting to know each other to become an ‘us’. All good relationships progress and grow; these milestones are an important part of that.

Find out when most couples complete these milestones and even more – all the way to tying the knot – from Match’s Dating Milestone report!

Elizabeth Sullivan is an experienced dating, relationship & life coach, her speciality is helping people attract a great partner. You can find her at and arrange a free 20 minute dating consultation

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