Labor Day Weekend Single Dating Tips

Happy Friday!  Yup, Labor Day weekend starts this afternoon for those of us in The States.  If you live in a city metropolitan area, you are likely finagling some way to leave the office early, earlier than usual in the Summer Time on a Friday.  When I worked in New York years ago during summer vacations while in college, Friday afternoon, many of the rank and file employees were finding ways to leave the office by 4:00 pm.  Many of them had brought their weekend get away luggage with them to the office, and they would leave for their weekend adventures directly from the office.

In Manhattan where most of them were going were The Hamptons or Provincetown to go enjoy the beaches, crafts fairs, and local ambiance.  They would aim to catch The Jitney when it was picking up passengers further uptown and not meet it at its starting point in (roughly) midtown Manhattan.

Well, on major holiday weekends, everyone was maneuvering to get out of the office by 3:00 pm to get a jump on the traffic.  Even those of us earning only an hourly rate wanted to get moving early and beat the worst of the traffic for all of our fun destinations, too.  Traffic would always back up on the L.I.E. on long weekends.  But when someone else was driving, it was bearable.  And yes, I used to bop out to The Hamptons as well.  We had relatives in Southampton, so we got to enjoy the best beaches around out on Long Island.  We even brought along our bicycles for exercise and transportation.  Yes, The Jitney takes (or at least took), bicycles.

So this is my little reminder to all singles who are not dating at least 3 others in the Getting To Know You stage of dating and courtship, take advantage of the planned movement and travel of many others including singles and get out there and socialize this weekend.  Yes, it’s so fun when you can plan a little trip yourself and go somewhere fun and at least a few hours away this weekend.  And certainly the economy will thank you for that shot in the arm of your money transfusion.  However, maybe you didn’t make plans and here it is already Friday.  It’s a little late to make plans.  There is always Las Vegas and you can still probably get some good deals and find a room even at the premier world class hotels along the strip.  Check out deals on line and give them a phone call.

However, if you’re not going to go away for the weekend, you can even manage a little day trip around where you live and stretch yourself socially.  Is there a small resort town of any kind near where you like that is, say, within an hour to two hour drive of where you live?  Make it a little road trip, pack your sunscreen, and wrangle up the company of 1 or 2 of your fun close friends and go!  You don’t want more than 1 or 2 friends, because groups up to about 4 people is all that most strangers will approach and talk to.  Single guy or single gal, you want to be approachable to strangers.  Pack a cooler and go to a local beach, Park, or even with the humongous crowds that will be there this weekend, an Amusement Park.  The crowds and long lines actually help to foster conversation.

What are some of the easy conversation openers you can safely ask just about anyone without being impertinent or invading their privacy?

Where are you from?

Are you visiting here on a vacation or are you a local?

Do you have any extra sunscreen?  I can’t find mine.  (Perfect at that beach or at an Amusement Park.)

You can get the ball rolling with at least a few sentences.  3-5 sentences is just about always my rule to test the waters to see if they will respond and engage in conversation with you.  Now, if you are on line with them for a ride, you will likely be lightly conversing for at least 10 minutes.  Keep your tone pleasant, not badgering, and just remain pleasantly casually interested in them, their friends, the people behind them on line, and the person on the other side of you.  You are just engaged and interested.  Now if you are all young and single, you are probably particularly geared up for wanting to flirt with opposite sex and maybe hang out for the day.  Over 35 years old, and you and the others likely are interested in each other, but not in that Spring Break urge to gaggle manner.  So, if there is the slightest spark, give them your personal card, ask for their phone number and invite them to share a soda or coffee with you after the ride is over.  Be sure to be clear about where to meet at the end of the ride, or you might lose each other inadvertently.  If they are with friends, be sure to include them in some manner because they are unlikely to ditch their buddies, both out of being polite and for safety reasons.

Your goal while here is just to take things to the next level of being acquainted.  This is a mini-Date.  A Datelette.  You want to converse and flirt, and just get a little better acquainted and maybe sneak a kiss and see if you two want to meet for a full fledged date another time.

Start brainstorming for where to go, even if it is just a different Watering Hole for Friday Night Happy Hour with a few different friends than the ones you always hang out with.  There are often cute cities with great restaurants all within just about an hour drive of where you live.  Take a friend or two along with you, be the designated driver, and you’ll qualify to drive in the H.O.V./Commute Lane and shorten the drive even more.

Go ahead.  Challenge yourself a little.  How many new people of the opposite sex can you meet tonight and exchange a few sentences of casual conversation with?  Shake things up a little, stretch yourself, and have some fun this holiday weekend!  That’s the whole point of Labor Day.  To honor your hard work and take a little much deserved break.  You’ve earned it!

Happy Labor Day weekend!

Happy Dating and Relationships,

April Braswell
Dating and Relationship Expert

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April Braswell

April Braswell is internationally recognized as America's Midlife Dating and Relationship Mentor and the award winning expert columnist at DatingAdvice.com. Bringing over 40 years of Sales and Marketing expertise, April is a the trusted Small Business Consultant and Coach to Leading Executives and Emerging Leaders. Author of best seller, Get Swipe Right. April coaches marriage-minded men and women to find and attract love, your best life partner. Life Love Love relationship. Love after 40 and 50. Photos appear by licenses with iStock. All rights reserved.

Reader Interactions

Comments

  1. Hi April,

    Good to see you talking about great actions that singles can take right now this weekend to improve their social lives, have fun and meet people.

    Who wants to be sitting at home when they could be out with people. One more note, in much of the country– high school and college football games are gearing up this weekend. High school games are a great community event and lots of people there cheering on the locals…

    Most college campuses have major tailgating things going on and you can participate for the cost of a parking pass. Bring some beer or wine in a cooler and something to cook on a grill, and go the lot and find a group of people with a hot grill and ask them if you can please cook your lunch on it…

    Instant friends, and they are probably in a great mood… who knows someone might even have extra tickets…

    Seize the Day,
    Survival Rob

  2. April,

    You have some excellent ideas there… for singles who want to get out, mix, get to know folks, have fun….

    Labour Day is a great day… but a little sad – as it kind of marks the end of the best season of the year: summer – It’s back to work!

    Well, there’s always weekends to look forward to…! and social media!

    Happy Labor Day to all who celebrate it?
    Eileen

  3. Hi April!
    Very interesting reading your tips!
    I think it is quite different the way americans and europeans date and go out for fun. Even here in Europe depending from what country you are what you will do to approach a person you don’t know can be as far as the moon from the sun!
    I’ll try to learn from you the american way!

  4. I really enjoyed this post, some great ideas for getting the conversation rolling without being too obvious, or feeling too awkward. And you make a great point about getting out there on a holiday. Anyone who has been single for any length of time knows how easy it can be to get into a rut.. and how much more fun and interesting your life can be when you force yourself to get out and about.

  5. April,

    These sound like some great ideas, but they’re about 30 years too late for me. 🙂

    Having said that, if I’d known this sort of stuff when I was 20, I maybe wouldn’t have got into my first, disastrous marriage – but then again, I probably wouldn’t be where I am today, happily married to my second wife, and doing something much more rewarding in life.

    And I can’t see either of us getting out this holiday weekend – not only do we have to be on hand for our customers, to whom we offer 24 x 7 phone support, but we actually don’t go anywhere ever (the last time we went out, other than to the mail box at the end of the road, was March 2007). To say we’re reclusive would be an understatement.

    Rae & Mark

  6. I chuckled reading this as I was thinking about my single friend who takes a “date maker” on the train with her. It is a small cooler with pop and beer. She will sit next to a person of interest and pop out the date maker and the rest is history.
    Yours In Health!

    Dr. Wendy M. Schauer, D.C., R.K.C.

  7. Hi April – have you ever considered adding more dating tip videos to your blog posts to keep your singles readers more entertained? I mean I just read through the entire article of yours and it was quite good but since I’m more of a visual learner,I found that to be more helpful well let me know how it turns out! I love what you guys are always up too. Such clever work and dating and relationship reporting! Keep up the great works guys I’ve added you guys to my blogroll. This is a great article thanks for sharing this informative information.. I will visit your blog regularly for some latest post.

  8. Hi April,

    This is such a great dating tip for single men and single women. Don’t you find that to test the waters whether the other dating single will respond, just tell about yourself in a few sentences without self boosting?

  9. April, I agree absolutely, I love it. What interesting and well-founded dating tips for singles. Good reminders to get out and meet others in the wisdom of your words. Please write more interesting dating articles in your web-site.

  10. I want to take this moment to say that I really love this blog. What an excellent reminder for us singles to get out and about on the holidays. It has been a good resource of information for me in my research. Thank you so much.

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