First date etiquette for widows and widowers

Last updated on 6 December 2023

Image source: For widows and widowers who thought about today’s dating scene and considered putting themselves out there, just know that you shouldn’t feel guilty. [Source: Shutterstock]

Key points:

  • The modern dating scene might seem unusual compared to when you first met your partner, but this edition of Your Retirement Living will offer some words of wisdom and encouragement
  • You might want to talk extensively about your partner at first, but it might be best to wait until a more appropriate time — simply informing your date of your widow/widower status might be sufficient for a first impression
  • Take this opportunity to overhaul your wardrobe and make an effort to look stylish prior to the meeting, so that your confidence shines through

This edition of Your Retirement Living will address how a widow or widower can get involved in the modern dating scene and prepare for their first date — topics include: self-reflection, digital dating applications versus meeting someone in real life, what to wear and intimacy.


People never forget their first break-up, which can feel like a crushing loss at a young age, but when a partner that has dedicated their life to you is no longer physically present, it may feel like an unimaginable pain that few will ever experience. Some people may never feel capable of moving on, which is perfectly normal and can be a healthy strategy for maintaining positive mental wellbeing.

Some people may feel that they are ready to move on, but after significant time has passed and a person has adjusted to feeling alone, it is also natural to feel lonely. Naturally, the cure to loneliness may appear to be other people, which is actually something of a misnomer. You can feel loneliness in huge crowds, but find comfort in being by yourself, for instance.

If you are looking for social affirmation and connection, you may find community hobbies such as sports, social clubs and volunteering to be far more beneficial than trying to break into the dating world. However, if you feel that it’s your time to shine — take your time to make sure that you leave the best first impression.

Remember: rejection does not equal failure, it just means that you have to give it another shot.

Meeting online or in-person?

When you meet someone out in public or throughout the course of your life, you never know whether they’re looking for a relationship, whether they’re looking for a relationship with you or whether you would enjoy the company of that person at all.

This is why many people choose online dating as a viable dating option, through apps such as Tinder and Bumble [all preferences] or Grindr [for specifically the LGBTQ+ community].

Here are the positives and negatives of mobile dating apps:


  • There are a lot of people on these platforms, so you’ll have many potential opportunities to meet someone
  • Rather than trying to come up with a response to “tell me about yourself” on the spot, you can take your time to come up with something clever
  • You can choose your photos and get creative with visual self-expression
  • Some apps give you opportunity to put forth your preferences and deal breakers, such as a person’s smoking status, drinking status, children or pets they may have
  • You can get to know a person a bit and build up a bond comfortably before meeting them
  • Some apps have paid features to see people that have expressed interest in you, to cut down on rejection and see your options
  • You can include your widow status in your profile or tell potential partners about it in a less intrusive way, so that they know what they’re in for


  • The rate of rejection is very high due to the number of people on these platforms — don’t worry — that’s across the board, don’t take it personally
  • There’s an increased likelihood for scams and you may find people who don’t use the platform to find love — a practice known as ‘catfishing’
  • People tend to be nastier online, so you may encounter some unwelcome comments 
  • Meeting someone in real life after only knowing them online can be particularly awkward, especially if you’ve discussed anything intimate
  • You have to wait to hear back from the other person, which can take far longer than a call or in-person meeting
  • People tend to lie about things online, like their age, profession or even their past

What to wear on your first date

Style advice for a first date is abundant online — ‘dress classy,’ ‘dress stylish,’ ‘dress in an eye-catching way,’ et cetera.

Meeting a person for the first time or on a first date should reflect two things, regardless of gender: enjoying time between two people and self-expression. Let your clothing tell a part of your story and demonstrate that you put time and effort into meeting the other person.

Wearing clothing that you feel comfortable in will open up your personality and allow you to feel more confident with yourself in a setting which many often consider to be awkward or uncomfortable. Additionally, it is important that your clothing serves as a litmus test of your future with the other person — as their attitude towards your clothing may be a deal breaker for you in the long-run and it’s best to ‘rip the Band-Aid off’ sooner rather than later.

Intimacy — what we say and when we say it

‘Intimacy’ as a concept has become synonymous with sexual intercourse, but there’s far more to the meaning of the word than physical interaction. Intimacy can also refer to a sense of confidential and emotional connection.

For an event as traumatic as the loss of a partner, you may want to overshare on the first date impulsively, which can potentially scare someone off, particularly if the intimate story was said unprompted. Others, however, may cope with loss and hold their memories close to their chest, which may also be a risk to the future relationship over time.

It’s okay to move on and not let go, so long as you go at your own pace and ensure that the other person is able to keep up with you. It may feel as if no one knows what your experience is like and many people don’t — so it’s important to let them know what you’re okay with talking about as well. Find comfort in the idea that the other person is keen to enjoy their time with you as much as you are with them.

Some top tips for good behaviour on a first date

  • Make an effort to pay for food, drinks or activities; at least attempt to split any costs, in lieu of outright payment.
  • People have said more to a person on a date through listening than they have through speaking
  • Make eye contact when you speak
  • If alcohol consumption is likely on a date, have one glass of water between each drink or two, in case of a cocktail venue
  • Refrain from outright declaring opinions, particularly on the other party
  • Suggest plans rather than invite someone to your plans — some people may not like coffee, drinking, eating in front of others or going to see certain genres of films at the cinema

Recommended ice-breakers

  • “Which animal do you believe enjoys their life the most?”
  • “How was your week this week and how did it compare to last week?”
  • “If you were to rate today’s weather based on how much you like it, with a highest possible score of 10, how would you rate it?

What are your thoughts and tips for a first date?

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