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Tips for successfully dating later in life

Dating can be stressful, nerve-wracking, awkward, and also very exhausting! But dating can also be exciting, rewarding and a great way to meet new and interesting people.

Last updated: April 25th 2022
Do a “stocktake” of your past relationships and work on yourself before entering a new relationship or start dating again. [Source: Shutterstock]

Do a “stocktake” of your past relationships and work on yourself before entering a new relationship or start dating again. [Source: Shutterstock]

Key points:

  • Be aware of what you are looking for in a relationship and how that will fit within your current life
  • Take your time to find a new partner and don’t ‘settle’ for the first person you come across
  • Try not to take past relationship baggage into any new relationships

If you have been out of the dating scene for a long time, it is not surprising you may feel out of practice trying to get back into the swing of things in your later years.

Where marriages fail or you lose your partner, it is natural to seek connection and intimacy with others.

According to Clinical and counselling psychologist Elisabeth Shaw, Chief Executive Officer (CEO) of Relationships Australia New South Wales, it can feel like you haven’t been on a date in decades if you have been in a long-term relationship up until your 50s, 60s, or 70s.

Ms Shaw says it is important to take the time to re-partner in life if that is what you want to do and you should never “settle” when finding a new partner.

“If being in a relationship or having those intimate connections is important, stand up for those connections and pursue them regardless of what others say,” explains Ms Shaw.

Since dating can be nerve-wracking, Ms Shaw has provided five tips on how to have good dating experiences:

Tip 1: Repair the past

Before getting back into the dating scene, Ms Shaw recommends you take stock of your past relationships as many people can end up taking in past “baggage” into new relationships.

And it’s not uncommon for people to either put their walls up while dating or to project past problems onto new partners.

“I think this is important for people at any age to reflect on their relationship history and really look at where they are at before they enter the dating scene,” says Ms Shaw.

“Too many people don’t think about that enough and they unconsciously carry it into the next relationship. You really have got to resolve and let go of some of that in the past.

“It’s virtually doing a stocktake of where you are up to.”

If you are able to let go of past relationships, it will result in more fruitful dating with new people.

Tip 2: Work on yourself

Wanting to find a connection can be really important and worthwhile at all ages, however, you don’t want to use a new partner as a safety net or a way to make yourself feel better.

Ms Shaw says that relationships should be the “icing on the cake, not the cake”.

Working on yourself, your confidence and who you are as a person means you are bringing a whole lot more to the table and aren’t “settling” for the first partner you come across.

You shouldn’t be seeking a new partner to make yourself feel complete as a person but to add to the happiness that you already have.

“If you are feeling lonely and you don’t have enough friends, and say you have lost your partner and your life feels really empty, it is much better to do work on the emptiness and develop the friendships you need for that life stage than it is to rush straight to an intimate partner as if they are going to fill that gap,” explains Ms Shaw.

“It also makes you more of an attractive proposition because it is more attractive for someone to join a full life than it is to feel like they have come along to rescue you.”

Tip 3: Know what you want in a relationship

After many years, you should be pretty aware of what you like and don’t like in a relationship.

You should be having open conversations with a person about what you are looking for in a relationship and whether that makes them compatible with you.

For instance, you may be keen for someone who is outgoing or pushes themselves by trying new things, or if you are a homebody you may prefer someone with a similar temperament.

Just because a relationship match works doesn’t mean it is right.

You should be looking for a person that matches your goals, aligns with your beliefs and interests, and improves on the good life you have.

“You could end up really liking someone and for whatever reason, they don’t fit with you. Having a good time, whether you are ‘chosen’ or not, is just as important as trying to connect with that human experience,” says Ms Shaw.

Tip 4: Set boundaries

A new relationship can be a good time to set personal boundaries with a new partner so you are comfortable and respected in your new relationship.

Setting boundaries early means the expectations for dating are front and centre from the get-go, so not only do you feel comfortable when dating but it can also help you know if the person you are seeing will respect those boundaries.

Ms Shaw explains that it may be a first date with you but the other person may have been dating for a while.

“They may be much more advanced in what they are looking for and in fact might be looking for something different, like something more casual or a sexual relationship.”

“Be confident about how far you are prepared to go. Even if you say no to something and go home feeling like you have lost a lot by saying no, that is where having people in your corner, a cheer squad or people you can go back to debrief the experience, is important because being able to say no when you need to is really critical.”

Tip 5: Don't shy away from awkward conversations

Having an awkward conversation with a new date or partner will be pretty common in the early stages, however, you shouldn’t shy away from having them if they are important to you.

While younger couples will be looking at questions of marriage or future children, for older adults it can bring up conversations around prenuptial agreements and estate planning.

“The normal trajectory of a relationship we are all trained into is you meet someone, you fall in love and you move in together, and you marry them,” explains Ms Shaw.

“In the older age groups, particularly if people have been divorced or they have built a legacy that they want to preserve for their children, they may not want a situation where they may have to divide their assets again or compromise inheritance.

“Sometimes at that life stage, involving prenuptial agreements and lawyers can be more common. People have real hesitancy [having these discussions], it sounds unromantic but it doesn’t need to be at all.”

Ms Shaw says some older people are worried about dating because they don’t want to discuss estate planning, merging assets, or living in the same house.

However, wanting a relationship with “all the good bits and not the other bits” is a perfectly fine way to arrange a relationship.

Just make sure there is open and honest communication between both people in the relationship about how you would like to structure the relationship.

What are your go-to first date ideas and how do you ensure a good first date? Tell us in the comments below.

Related content:

Dating when you’re older: how to find that connection
Dealing with the loss of a partner
The freedom of growing older


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