Ready To Date Again?

After years with a spouse, diving back into the dating pool can be scary. Here’s advice on how to start.

by Caitlin Ascolese

t’s one thing to finally feel ready to rejoin the dating world after a divorce or the death of a spouse, but actually making those first baby steps to do something about it is a whole other story. “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 key steps for putting yourself back 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
Get comfortable by practicing small talk whenever possible.
good way to see what the whole scene is about. 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 a taste of how it all works,” says psychotherapist Tina Tessina, Ph.D., author of The Unofficial Guide to Dating Again. “Look at the profiles—both men and women’s.” That’ll show you who’s out there… and 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 onto how other people describe themselves, which is useful when you’re ready to write 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 again,” says Dr. Riche. “Start by going out with friends and then joining activities with both sexes.”

“Finding groups online is a great way to get to know people and find interest groups,” says the recently remarried Karen Abraham, who founded 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% ready for a serious relationship.” Sign up for stuff you’re genuinely interested in—you’ll get more comfortable making small talk there, and pursuing your passions gives you more to talk about on a date.

Rehearse the tough stuff
Being a widow, widower, or divorcée 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 for a date until you’re ready to. Other than giving the types of brief explanations you’d offer up to, say, a new co-worker (“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 OK place to date again,” says Russell Friedman, co-author 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.”

Of course, when you and a date have both survived a dramatic event — a
Don’t reveal details about your past until you’re totally ready.
divorce, a death — it’s natural to bond over that. But when two people share an overload of information, they often mistake it for compatibility and rush into a serious relationship. So have a line in mind to steer too-intense conversations back to safe ground. 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 continuing to get to know your date.

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 great date destinations to what it means when a date says he or she will call and then doesn’t, these are the people to rely on. “Take advice from a friend who’s dating the way you’d like to, not a friend who you feel is too casual about sex or one who juggles multiple suitors if you’re a one-person-at-a-time type,” says Dr. Tessina. Ask for help and input—these people are likely to feel flattered to be your relationship coach!

Outsource your options
Once you’re ready, launch a word-of-mouth marketing campaign for your hottest product: yourself. Let people in your life know — friends, co-workers, people at church, your trainer, the folks at that new knitting group you just joined to practice making conversation — that you’re looking to date and ask them to keep you in mind if they know 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 wing-women, the more quality prospects you’ll have to choose from.

Bring the sexy back
Remember when you used to actually get dressed up to look good for a person of the opposite sex? It’s time to get out there again find a few key items that make you look and feel amazing. “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 buying yourself something new is nothing compared to how self-conscious you’ll be if you feel unattractive while you’re out with someone you want to impress.

Take your time
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 a new single, 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 because you’re widowed or divorced. It’s a natural occurrence for all singles, so take it in your stride. Your new identity as an available, amazing single allows plenty of opportunity for you to try out a week or two or more of mingling while you recharge your romance batteries!

Caitlin Ascolese is a freelance writer in New York City.
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