Baby Boomer Love:
Ready to Date Again?

It's one thing to finally feel ready to rejoin the dating world after a divorce or the death of a spouse, but actually taking those first baby steps to do something about it is a whole other story. It's a lot to grapple with: How are you supposed to meet people? What if people think you're dating too soon -- or too long -- after your marriage? How do you explain why you're single? What do people even talk about on dates?

"Going from being married to single again can be an identity crisis for many people," says life coach Anthony Riche, Ph.D., author of 'Finally! How to Stop Dating Losers Forever.' "You may feel like you’re back in high school having to 'relearn' how to date again, but there are steps you can take to regain your confidence." That's why we talked to experts to find out the biggest concerns freshly-singled daters have, and came up with this list of seven crucial steps -- any of which you can start doing today to put yourself on the road to romance.

Browse Around
With millions of members, dating sites aren't just a good way to meet people, they're a good way to see what the whole dating scene is about right now. On many sites, you can create an account to browse from without having to put up any information at all; others offer free trials. "Sign on and get acquainted with what's out there -- and who's out there," says psychotherapist Tina Tessina, Ph.D., author of 'The Unofficial Guide to Dating Again.' "Look at the profiles -- both men and women's -- to see how it works." Looking through the list of available partners can give you an idea of just how un-alone you are in the quest for the right relationship. And scouring ads of people of the same sex can give you insight into how to craft a profile. You'll start to see what works and what doesn't for both sexes: the types of profiles that look careless or clichéd, vs. the descriptions that really come alive. Put that info to use when you’re ready to craft your own profile.

Practice, Practice, Practice
Being charming on a date is easier when you’re already used to being charming in real life. So before you get out there one-on-one, remember what it's like to meet, greet, and get to know strangers. "The key is becoming comfortable being social and open again," says Dr. Riche. "Start by going out with friends and then joining activities with both sexes until you're used to having conversations and interactions with strangers."

"Finding groups online is a great way to get to know people and find interest groups," says the recently re-married Karen Abraham, who founded YoungCancerSpouses.org after her husband died when she was 28. "You can balance being social while you nurse crushes or even find people to, as I put it, 'practice date' until you're 100 percent ready for a serious relationship." Sign up for stuff you're genuinely interested in—whether that's a wild and crazy bowling league or a local political volunteer group. Not only will you get more comfortable at making the right kind of small talk, you’ll have lots more stories to talk about on the date. Another plus: "Even if your group is all women, they may have brothers or friends or husband's friends to set you up with," says Abraham.

Rehearse the Tough Stuff
Being a widowed or divorced is no picnic, but the thought of having to answer questions about it adds extra pain. The good news is, you don't have to (nor should you) unpack your past on any date until you really trust the person and want him or her to know the details. Other than giving the types of brief explanations you'd offer up to, say, a new coworker who asks over lunch about your status ("I was recently divorced" or "I moved here with my late husband"), you're off the hook. "A simple statement can let your date know the facts, and that you've found closure and are in an O.K. place to date again," says Russell Friedman, coauthor of 'Moving On.' He recommends responding to any further questions with a line like, "I've done a lot to deal with the impact of that relationship, and I feel ready to get out there again." The only time that won’t work? If you actually haven’t found closure, in which case your nonverbal behavior, whether it’s gritting your teeth at the mention of your ex or breaking down over how great things were with your late spouse... so don’t try to fake it.

Of course, when you and a date have both survived a dramatic event -- a divorce, a death, the cancellation of a favorite TV series -- it's natural to bond over some of what you went through. But rehashing the drama often gets too personal, too fast. The danger is that when two people share an overload of information, they often mistake it for actually being compatible and rush into a serious relationship. So have a handy line in mind to steer these conversations back to safe ground if you find yourself thinking, "This is getting too deep for a first/third/whatever-it-is date"). Friedman recommends something like, "You know, that might be a little more detail than I’m up for right now." It's simple, honest, and shows that you're interested in getting to know your date, not just his or her baggage.

Reconnect with Certain friends
Remember all those non-hooked-up friends who never came to couples' nights and got bored every time your talk turned to problems with the kiddies? Those same pals can be your best allies right about now. From the best places to go on dates to the most common uh-oh's to watch out for to what it 'means' when a date says he or she will call and then doesn't, they get it. "Take the advice of a friend who’s dating the way you'd like to do it, not a buddy who, say, sleeps around if you're not into that," says Dr. Tessina. Remember these people have been living and breathing the life that you're just re-entering. So ask them for help and input -- they'll likely be honored to feel like the relationship experts for once.

Outsource Your Options
Once you're ready, launch a word-of-mouth marketing campaign for your hottest product: yourself. Let people in your life -- friends, coworkers, people at church, your trainer, the folks at that new knitting group you just joined to practice making conversation -- know that you're looking to date and ask them to keep you in mind if they know or meet anyone great. "They're likely to try and set you up with the right person, they'll give you important information about the person, and you won’t find yourself fishing for things to talk about on that first date," says Dr. Riche. Remember, the more people you recruit to be your wingmen and women, the more quality prospects you'll have to choose from.

Bring Sexy Back
Remember when you used to actually get dressed up to look good for a person of the opposite sex? Yeah, it may seem like forever ago, and to be honest, those same confidence-boosting clothes probably don’t fit, have gone out of style, or will have disappeared to the dark recesses of your closet. So get out there and find a few key items that make you look amazing. It doesn't have to be a head-to-toe makeover; just a few pieces that highlight your best features or make you feel less self-conscious about your not-so-best ones. "How you present yourself to the world communicates how you feel about yourself," says Dr. Riche. "Find out what kind of message you want to send, and make sure your look represents that." However indulgent you feel going out and buying yourself something new is nothing compared to how self-conscious you'll be if you feel uncomfortable or unattractive while you’re out with someone you want to win over.

Take Your Time
Now that you've finally made a date with someone, the hard part is over and you can go back to being a couple, right? We wish. "Every date offers an opportunity for a new relationship, as well as the chance that this isn't the right one. The expectation that you'll meet one person, get together, and find intimacy and commitment is uncomfortable," says Dr. Tessina. "No matter how hard people try to make that work, it doesn't."Many singles go through cycles of being burned out by the effort required to put themselves out there and take 'downtime' from their dating life. When you’re newly single again, you may feel exhausted after only a date or two. So take a break as soon as you start feeling overwhelmed, and know that it isn't a reflection on you as a widowed or divorced person, it’s all a natural part of your new identity: smart, available, and amazing single.

Caitlin Ascolese is a freelance writer in New York City.

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