Dating can be daunting, no matter your age. But if you are at midlife or beyond, widowed, divorced, or just plain single, it can be even more challenging. Why do people with so many years of life experience under their belts find dating so intimidating? Here are some of the most common dating challenges along with solutions for people “of a certain age.”
1. Ready… Or Not?
One of the most common questions widowed or divorced people ask themselves is am I ready to date? Or more importantly, how do I know if I’m ready? Just as each of us has our own set of beliefs and values around dating, we’re also unique in how we define “ready.” For some, readiness is a function of what motivates them. For example, if you’re not comfortable being alone or having a single lifestyle, you may be ready to date sooner rather than later.
2. Dealing With Grief And Loss
For others, working through grief and loss is a top priority, and until that happens, dating is not on their radar. If you’re having difficulty coming to terms with grief and loss, you may want to seek the services of a coach or a therapist. Being stuck in the grieving process is one of the main obstacles to dating.
3. What About Guilt?
Speaking of obstacles, if you are widowed, guilt can be an additional stumbling block. You may view dating as a betrayal of your deceased spouse or partner. This is a complicated dynamic because unlike a divorce, where individuals separate by choice, as a widow/widower the love remains, making it difficult to connect with a new partner.
Guilt around dating is also common among divorced parents. Children of any age may view your dating as a blatant act of disrespect toward your ex, making it difficult to date with a clean conscience. Younger children often cling to the possibility of their parents getting back together, so a parent who dates effectively dashes those dreams. Plus, a parent dating may be seen as the official sign that their parent’s marriage is over.
4. You’re Ready… Now What?
Once you’ve decided that you’re ready to start dating, you may want to break the news to your family. Telling your children may be the most uncomfortable aspect of your decision. Here are some tips and strategies to help make it easier.
Honesty Is The Best Policy
I encourage my coaching clients to keep it simple, straightforward, and honest. You might not get the support or acceptance you were hoping for, but give it time. Keep in mind that although preferred, your children’s support and acceptance are not requirements for you to start dating. It’s about you, not them.
Prepare
Decide what you would like to say in advance, write it down and practice saying it out loud ahead of time. Rehearsal helps reduce any anxiety. Say what you want to say in a calm, emotionally neutral manner. Remember, you are not asking for permission. You are telling them what to expect.
Regardless of your children’s ages, keep it short and sweet. You do not have to explain or justify your decision. You can share a bit about how and/or why you arrived at your decision if you like, but it is not necessary. The more direct and to the point, the better. “Less is more.”
Respond Rather Than React
Your children may not be pleased with your decision. They are entitled to their feelings and opinions without rebuke. Listen attentively, so they know they’ve been heard. Assure them that dating doesn’t change your relationship with them and that if they want to discuss their feelings or concerns, you are there for them. Here are some additional tools and strategies for juggling children and dating.
Choose The Right Time And Place To Speak Your Truth
A crowded restaurant in the company of extended family or friends is neither the right time nor place. Tell your children ahead of time that you want to call a meeting to discuss a family matter. Resist the urge to give them a hint, as that may start the conversation prematurely. Reassure them that everything is okay. Conducting the meeting at home without distractions is preferable.
The same goes for telling others. It is not unusual for adults who know you well to offer unsolicited advice. They are usually trying to help, but the bottom line is that it is your decision. It is not up for discussion unless you want it to be.
5. Navigating The Brave New World Of Dating
If you’re relatively new to being single, it won’t take long to discover that dating isn’t what it used to be. Nowadays, online dating websites and apps play a larger role in hooking people up than ever before. Their popularity and success stem from their ability to solve one of the most
common problems plaguing would-be daters, difficulty meeting people. They provide a virtually endless supply of dating prospects, eliminating the need to find them on your own. Problem solved… or is it?
While dating apps and websites have their advantages, such as being easy and convenient to use, vetting of users, numerous profiles to choose from, and an increased likelihood of finding a match, they also have their drawbacks. IT security issues can put user privacy or safety at risk. Fake members, i.e. people who are not who they say they are, and profile pictures that don’t resemble the user are not uncommon. If you’re not computer/cell phone savvy, you may be up against a steeper learning curve. So what’s a single technophobe to do?
Soften The Curve
If you’re clueless about online dating sites/apps, but would like to give them a try, start by asking someone you know who is familiar with them to walk you through it. Take notes as you go along and ask for additional tips and strategies that might be helpful. Having a tutor can help you feel more comfortable, knowing you can ask for help if you need it.
Sleuth For Yourself
To err on the side of caution, you can conduct your own research to check out a dating prospect. The easiest place to start is with a Google search. At the very least, it may provide some general background information. There is no guarantee that your search will unearth any red flags, but you never know.
Social media platforms such as Facebook and others sometimes yield information worthy of note. It might be more difficult to gain access to them, but as a casual observer, you may be able to make some telling observations. Bottom line: if you’re not comfortable with the potential exposure or other downsides associated with online dating sites, they may not be for you.
6. Where To Begin Your Online Dating Adventure
Based on observations and feedback from my coaching clients, I suggest you check out SilverSingles, OurTime, eHarmony, Elite Singles, and Zoosk. Assess each site carefully, comparing options and features. For newbies, I recommend a one site at a time approach rather than a blitz to help you gradually learn the ins and outs of online dating and get more out of what each site has to offer. Once you’ve gotten your sea legs, you can more easily manage membership to more than one site at a time.
7. Meeting People The Old-Fashioned Way
But what if online dating sites and apps are not your thing? What if you prefer to meet people the old-fashioned way, face-to-face? Take heart, there are more old-school daters out there than you think. If you’re not averse to blind dates, put out an APB to your friends, relatives, and social network to keep their eye out for potential prospects. That eliminates the discomfort of meeting a total stranger.
Taking a class, going to the gym, or attending a lecture creates an opportunity for kindred spirits to connect. If you like to play bridge, chess, or Scrabble, host a game night at your place and tell your guests to bring a friend. Experiment by putting yourself out there in new ways like community activism or volunteering to expand your social circles. This can be done via Zoom as well.
8. Taking The Plunge
Bottom line: no matter what method you choose — technological or traditional — dating takes time and effort. For more information on how to date the old-fashioned way and deal with common pitfalls and challenges of dating in retirement, check out this great read. Yes, dating can be daunting, especially as a senior, but if you wait until you’re good and ready or until the time is right, it may never happen. Dating is like riding a bicycle. No matter how old you are, you never forget how to do it.
