One day, however — trust me on this — the will to live fully again, and even experience companionship, will arise. It’s hard to throw yourself back in the dating game after 30, 40 years or more. I tell those I counsel to look at it this way: Cherish your old relationship, but don’t let it sabotage your prospects of forging a new one. More than merely a widow or widower, you are a person with opinions, hobbies, preferences, accomplishments, social values, political views and a unique way of looking at the world.But the pointers I offer below can help ease your pre-game jitters. And if your feelings of guilt persist, see a counselor; you’ll want to resolve these thoughts before attempting to date again. As you think about how to present your authentic self, be selective about which of those attributes you share right away and which are best kept private until you get to know a new person better. Take some time to think about the type of new bond you’d like to establish.When I told one of my girlfriends about my new sex life, she said, "Good for you for getting back on the horse!"Another friend said something I took to heart: that as women, we can claim our pleasure without shame, that our sexuality is a gift to be proud of.Perhaps you’re ready to see the world and want to find someone who shares your wanderlust. The simplest is to ask friends if they know someone you’d enjoy meeting. Most people probably won’t think of suggesting this on their own (and if they do, they may hold back for fear of offending you).Or maybe a partner’s allergies compelled you to live without pets and now you’re ready to romp with a fellow dog lover. Factors that loomed large in the past—good looks, financial success, whatever—may pale in the present as you acknowledge the importance of a partner who is kind and supportive, or one who is funny and entertaining. If you’ve become a bit, er, casual in the weight, wardrobe or grooming departments, now’s the time to ratchet up your game. So actively encourage them to think of you as a single, eligible person.
Seek out a clothing consultant or personal shopper — someone who can advise you on a flattering look and help you pick out items to achieve it. Research shows that many opportunities come through our “weak ties,” or people we know largely in passing: hairdresser, chiropractor, a neighbor’s visiting sister—even your seatmate on a flight! Most well-known dating sites have a large contingent of “seekers” in their 50s, 60s and 70s (and some in their 80s and even 90s), and several reputable sites are now completely free.And you may also be plagued by feelings of guilt and uncertainty.And then there’s the reactions of other people to deal with – not least your in laws and your own children, if you’re a parent.The idea that we "should" only have sex within the context of a serious relationship was an antiquated judgment to be disregarded.And I agree, despite being raised conservatively by a widowed father who taught me that nice girls say "no."I eventually ended things with my friend. Fourteen months after George died, I decided I was ready to date. I did what I felt like regardless of any potential for a relationship. His opinions on sex apparently varied greatly when speaking to a 50-year-old widow as opposed to his teenaged daughter.