Tips for Better Dates


Every year Lisa and I look forward to our dating clinics where we meet with employees to talk about all things dating and relationships. We offer these as part of our annual February Relationship Series. Although we promote these in February, we can meet with employees anytime to talk about this topic. I thought I'd share some of our tips here.

If you are in a long term relationship and are beginning to wonder if this post applies to you, try adapting some of these ideas. No matter how long the relationship, partners never stop going on dates. Use some of these tips to bring intention to the time you spend with your significant other.


What do you talk about on your date?

That day listen to a podcast, a TED talk, or read an article; something that provides interesting tidbits or a story to share. Some suggestions for interesting podcasts: 99% Invisible, Stuff You Should Know, Memory Palace, Freakonomics.

Here are some posts with unique ideas for questions:

55 Questions to Break the Ice

25 Ice Breaker Questions

36 Questions to Bring You Closer

This is a great video on How Not To Be Boring

Create a list of questions to ask (review what you know about the person before to help come up with questions). If you're afraid you'll forget, put them in the notes section in your phone and you can always check it in the bathroom if you can’t remember.

For those in long term relationships: One especially busy week it seemed like my husband and I never had the chance to sit down and catch up when we did see each other. There are many times throughout my day that I experience or learn something that I make a mental note to remember to share with him. Unfortunately I've found that more and more I keep forgetting those small things. Knowing that we had a dinner date planned for the end of the week, I made a notes section in my phone of all the things I wanted to share with him, just a few words for each topic to remind me. When we were out at dinner I actually showed him the list somewhat jokingly, but we went back and forth sharing about our week as I had him select random choices from the somewhat cryptic list I had kept. I'd rather keep a list than let the opportunities for connection pass by.

Some of these suggestions for prep may seem like a date won't be genuine. But the connection and conversation that flows from these questions will be. The suggestion isn't to make a script of what to say, but to put in the effort to prepare for intentional bids for connection.


What to do on your date?

Think about activities that foster shared experience. In her book SuperBetter, Jane McGonigal explains how doing activities and moving together promotes synchronization, which in turn promotes empathy and opportunity for connection.

  1. Walk around the NCMA Museum Park or Sarah P. Duke Gardens (when it’s light out), pack a picnic
  2. Take a coffee walk: pick a coffee shop in an interesting neighborhood and get your coffee to go
  3. Tour the First Friday Art Galleries in downtown Raleigh or Final Fridays Art Crawls in Cary
  4. Play games together at an arcade bar or a location that offers activities like bowling, darts, billiards, minigolf… the worse you are, the more opportunity for laughs or to share strategies
  5. If you are going to a bar/brewery/coffeeshop/bakery make it more of an experience. Go when tastings are offered. Get a few small things to split up and try. I remember going on a first date to an amazing bakery where there was so much to try. My date just ordered coffee and didn’t care to look at all of the baked goods. What could have been a fun experience to try new things was downgraded to just another coffee date.

I’ve written a blog post on this idea, but I’ll summarize quickly here. Each of you make a list of four to five things you enjoy doing. Switch lists. Circle one thing that you would be willing to do from the other person’s list. Make a day out of those two activities (or more if you have time). It shows that you're willing to step into their world and it welcomes them to yours.

Make your first date a “zero date” – a concept Christina Wallace explains in her TED Talk.  Our main takeaways are: Keep the date short (meet for coffee or a drink) with a planned “out” or reason to keep the date short (“I am meeting friends for dinner but can meet you for a drink before”). In that short time figure out if this is a person who you would like to one day have dinner with.


Lisa and I wish you the best on your dating and relationship journey!


About Author

Katie Seavey Pegoraro

Sr Associate Work Life Program Manager

Katie Seavey Pegoraro supports employees with issues of stress and balance, providing tools and resources to cope when life feels overwhelming. Katie is a contact for those who may be coping with issues of mental health, substance use, or grief and loss. A young professional herself, Katie is a unique support to employees who are navigating the many life transitions that occur in your 20's and 30's.

Leave A Reply

Back to Top