Author: HairWeavings Editorial Team

I’m blessed with a close family. We enjoy one another’s company so much that we vacation together as often as we can. Since travel is my business, the planning often falls to me. After a host of trips, I have learned a few things and created this list of unbreakable rules.

Be Flexible on Scheduling

This is self-evident if some members of the family are school-age kids, whether that means kindergarten or college. They are slaves to the school calendar and likely will only be able to travel on school holidays. If you want them on the trip, it has to happen when they’re available.

Not being beholden to the school schedule, however, does not mean you are home-free. Chances are there will be some member of the family who has limited vacation time – a young adult who has just started a new job, for example, or an hourly worker whose work schedule is unpredictable.

I think it’s easiest to start with an online scheduling tool like this free Doodle scheduling tool. Everyone can add their own availability to at least narrow down the choices. Then you can move to a group conversation in person or via Zoom to finish the discussion.

Be Honest About the Cost

There are many ways to pay for a multi-gen trip. I’ve heard of families where Grandma and Grandpa treat everyone to the trip – one friend’s in-laws celebrated their 50th wedding anniversary by paying for their three kids, their spouses and all the grandkids to go on a Disney cruise.

And then there’s the way we do it in my family: Everyone pays their own way.

Both approaches have their benefits and drawbacks.

When the grandparents pay, it can mean they expect something in return: that everyone will show up, be happy and do what the grandparents want them to do.

When you do it the way my family does, it means some people have to compromise. We set the budget to ensure that every family can afford the trip. The wealthier families can treat themselves by booking a suite at the resort or taking themselves out to a fancy dinner one night.

Accommodate Everyone’s Needs

My mother-in-law is blind, and my father-in-law had some mobility challenges toward the end of his life, so when we decided on a family trip to an all-inclusive in Mexico, we chose the smallest one with the shortest walk to the beach and the calmest surf.

It meant that the teens had to compromise on a resort that offered fewer activities and amenities. But they got more time chilling on the beach, and we arranged for an off-property trip to swim in cenote.

Plan for Time Apart

It’s tempting to think that everyone needs to spend every minute together when you’re on a multigenerational family vacation. That’s why you’ve planned a trip together, right? Wrong! You planned the trip to spend MORE time together, but that doesn’t mean you need to spend ALL of the time together.

Everyone should be able to have the vacation they covet. While that might mean they want to spend every minute with you, never assume that is the case.

Always build time into the schedule during which each family member has the option of doing something on their own. The athletes can spend time being active. The couch potatoes can spend time lying on the beach. The youngest and oldest can spend time napping.

Having said that, remember that is supposed to be a family trip. That means it’s reasonable to require everyone to spend some structured time together – dinner each night or one excursion or activity you all agree to do together, for example.

Don’t Make One Person Do All the Work!

This is a lesson I learned the hard way. We were headed to a niece’s wedding in Dallas, so I agreed to squire around my husband’s 82-year-old mom, his 80-year-old aunt, hubby and our two teens for a 3-day tour of Dallas after the wedding.

After three days of managing six people, ranging in age from 15 to 82 – everything from getting them through airport security to managing museum entries and local transportation – I was completely exhausted. They, however, loved it. As we were waiting at the gate to board our flight home, they asked where we could go next.

I dredged up one more smile and responded, “An all-inclusive resort.”

What’s Your Experience:

Have you taken a multigenerational family vacation? What worked best for your family? What would you never do again?

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To give and receive love is a natural, universal desire.

Why, then, do most people feel awkward with self-love, choosing instead the unpredictable path of seeking love outside themselves?

Where does this need to rely on other people to validate our worthiness to be loved come from? And how can we begin to love more of ourselves after 60, despite how uncomfortable it may be at first?

We are going to answer these questions and more as we begin part two of my new six-part series on “The Art of Self-Love After 60”. In this series, we are focusing on ways to stimulate love, bliss, and pleasure on our own terms.

If you missed the first article in this series, please read 7 STEPS TO TURN UP THE HEAT ON YOUR LOVE LIFE.

Love Yourself Like No Other

The pursuit of love outside of ourselves is deeply entrenched into the psyche of society. It has gone on for so long that many are unaware of the extent to which they forsake their own well-being to be loved and wanted by others.

Being in a loving relationship with others can create extraordinarily joyful experiences. But when we place our sense of self-worth in the hands of others, we become separated from the one person who can love us like no other.

That would be our own self.

Our innate ability to love ourselves is incredibly powerful. For this reason, love has been widely distorted and manipulated in society as a means to disconnect us from who we are, forcing us to unknowingly give away our power to love without limits.

To restore our natural connection to the power of love requires that we individually rewrite the stories about what true love is and where it can be accessed.

Is There a Price on Love?

The basic premise of the stories about love we have been sold on as true stretch back to early childhood. Most of them carry three themes:

Theme 1

To get what you want, you must follow the rules of life, as they were instilled in you as a child. If you disobey, you will not receive the love you desire nor will you feel the safety, security, and value of being loved.

Theme 2

Love can be given to you, and it can be taken away from you. This is intricately tied to the first theme, producing a belief that love is something you must sacrifice yourself for in order to earn your right to have it.

Theme 3

Love is scarce and fickle. One moment love is like a fairytale delivering pleasure and bliss, whereas the next moment love is akin to a nightmare. In that scenario, love appears to be missing, producing acute pain and deep sorrow.

When you begin to connect the dots between these themes and your experiences with love, you begin to realize there is a steep price to pay to give and receive love.

10 Steps to Feel Worthy of Love

What if you didn’t have to pay a price for love? What if all you had to do to have access to the power of love is to stop believing love is outside of you?

With a mindful approach to self-love, these 10 steps can help you foster your own inner sense of well-being and nurture the love you seek from others from within.

Reframe Self-Talk

Identify and challenge negative thoughts and limiting beliefs about love. Replace these with positive affirmations.

Practice Self-Compassion

Treat yourself with as much love and compassion as you would treat your lover or a close friend. Show love, understanding and kindness to yourself, especially when you encounter mistakes or setbacks.

Set Healthy Boundaries

Ensure you are treated with love and respect in all of your relationships, including the one you have with yourself.

Stay Socially Connected

Join groups or communities that uplift and support women. Engaging with others, online and offline, can boost feelings of self-worth and connectedness.

Counseling or Therapy

A professional therapist or counselor can provide timely guidance on navigating feelings of unworthiness. They can also offer proven strategies to build your self-esteem.

Rediscover Your Passions

Engage in hobbies and activities you love. This not only boosts your self-esteem and strengthens your worthiness for love but also opens you up to meet like-minded individuals.

Stay Physically Active

Exercise is not only good for physical health but also mental well-being. It boosts your mood, increases energy, and creates a healthy, positive self-image.

Dress Confidently

Your outfits are not about dressing to impress others but wearing clothes what make you feel confident, happy, and sexy.

Seek Stories of Inspiration

There are countless stories of women over 60 finding love, embracing change, and starting new chapters. Seek out these stories for motivation. Sixty and Me is an ideal place to start.

Educate Yourself

Read books or attend workshops on self-worth, relationships, and self-love.

Remember that age doesn’t define one’s worthiness of love. Everyone is deserving of love, joy, and happiness. None more so than you.

I invite you to join me in the video above where I share five bonus steps to self love as well as guide you through three journal prompts to integrate what you are learning.

Let’s Have a Discussion:

Does it feel uncomfortable to love yourself? How are you loving more of yourself after 60? What resources have helped you on your self-love journey?

Considering our cultural norms, men traditionally make more money and are more highly educated than women who were born in the 1950s and earlier. Although today more women than men are pursuing master’s degrees, men are still making more in the workforce. As a result, it’s easy to see how women can find themselves in a situation where they are dating UP! But is it all rainbows and cotton candy?

Unbalance Can Cause Insecurity in a Relationship

Yes, there are other social currencies that can cause a sense of unbalance within a relationship, but financial success is the most popular. Of course, it’s fun to date a man who can afford to take me to nice places, but I don’t drive a Porsche or live in the Upper East Side in New York, and personally find mismatched levels of financial success polarizing in dating.

I’m a smart woman and realize that 85 percent of the things I worry about will never happen. However, that doesn’t stop me from letting crazy thoughts swim around in my brain. These are some of the things I needlessly worry about when I date someone at a higher income level:

• How can I spruce up my wardrobe – quickly? I’m almost 6’ tall and can’t buy much off the rack.
• Will his idea of travel exceed my budget?
• When we talk about money, am I confident enough to be honest about our socioeconomic differences?
• What will his sisters think? He may not know, but they’ll know what’s designer and what’s not.
• Will he think less of me because I’m in a lower tax bracket?

Of course, all these worries are ridiculous because I would never date a man who uses money as a romantic benchmark. However, it does highlight how insecurity can dampen the sparkle of a budding relationship.

Dating within Socioeconomic Status

Dating within your own socioeconomic status can naturally feel more comfortable for several reasons. You may find yourself seeking a partner with a similar background because you feel that they’ll also share your values and lifestyles.

Shared Values and Goals

Men and women from similar socioeconomic backgrounds often share similar ideas on how to enjoy their retirement years relating to their spending habits, lifestyle and travel preferences. This can create a sense of understanding and compatibility that makes relationships easier to navigate.

Access and Exposure

Unless you’re dating online, you may tend to meet men through social circles or communities that reflect your personal interests which are typically within your socioeconomic level. This limits how often you may meet men above those limits. However, if you’re dating online, you never know if you’re meeting a prince or a pauper until you get to know him.

Cultural Norms and Expectations

Societal norms and expectations can influence who you feel comfortable dating. However, if you’re like me, all the pressure I felt was self-induced.

What You Consider Practical

A similar bank account tends to correlate to similar life experiences and resources. When it does, it can result in a more balanced and stable relationship. When someone is at a higher income level it can be difficult to understand and accept their opposite point of view on emotionally charged issues like money.

Personally, I shook my head when I heard that my date purchased 100 pairs of lululemon yoga pants for his daughter at $98 a pair. I couldn’t wrap my head around why that was so important.  

Perceived Compatibility

Because your perception is your reality, you may naturally gravitate to men from a similar socioeconomic background because you perceive them as more compatible. The halo effect makes you believe that because you share some things you naturally share all things – which isn’t true of course, but our brain does move in that direction.

What Other Social Currencies Exist?

Even though money is the most common, there are other social currencies that can lead to someone dating UP. These include things such as education level, appearance, social circle, etc. In many cases, it can be hard to build a foundation with someone who appears mismatched to you according to social norms.

You may find at this stage of life it’s easier to create a happy, healthy, loving relationship with a man who is easy to flow with. This means he’s fairly matchy-matchy. He has similar interests and values, as well as being generally as attractive, intelligent and/or educated as you are. Is there scientific research to support this? No, but it seems as if it would be easier to create the right chemistry with someone who has a more aligned lifestyle. And regardless of his bank account, you still want to connect with someone who adds meaning to your life and shares a sense of deep emotional intimacy.

Expect It to Be Harder

So, don’t be surprised if when you date Up – or Down for that matter – that it’s harder than you expected. You’re melding lifestyles with someone you don’t relate to in a natural way. This applies to levels of intelligence, social skills, appearance, etc. The bigger the chasm at the beginning of a relationship, the more blending you’ll need to do.

In the end, relationships are about so much more than money, looks, or education. They’re about finding someone who gets you, supports you, and makes life better just by being there. Every relationship is unique and shaped by what you both truly value. It’s about finding someone who shares your passions, respects your goals, and makes your heart skip a beat whoever that may be.

Want to learn more about dating at this stage of life, click here to join my email list and receive my free newsletter. In the meantime, keep your heart open and ready for love.

Let’s Have a Discussion

Would you date someone in a dramatically different socioeconomic level than yourself? What about someone who is more/less attractive or educated. How much does ‘packaging’ matter in dating at this stage of life?