You’ve made contact with someone who sounds promising. You’ve followed up with some degree of vetting by chatting online or by phone, trying to get some idea of the accuracy of his profile. Now it’s time to meet. Don’t let him pressure you into a getting together till you’re ready—still, if you delay too long, your prospect may lose interest.


Never let someone you have found on the Internet meet you at home or in any other place where you could be vulnerable. Indeed, at this point he should not know where you live; some experts recommend that you don’t even volunteer your last name. Sure, you can swim in the ocean alone, with no one watching, but you just might drown.


 


 Just a Hello, and Not at Night


It’s a good idea to make your first meeting less of date and more of a hello. Choose a casual, neutral public place like a coffee shop; I believe that this setting lessens the pressure. For one thing, it relieves you of the burden of having to dress up; most important, a casual meeting in a public setting wil let you get away quickly if you are not comfortable or you know instantly that this guy is not for you. Have an excuse ready before you go. (“It’s my friend’s birthday, and we have plans,” or whatever.) On the other hand, if you hit it off and are having a great time, you can always extend the get-together by going for a walk, etc.


Also, for these reasons, and for safety, it’s best to plan to meet him in the daytime.


 


Sex


Meeting during the day has another virtue:  It finesses that all-important and sticky issue, sex. No matter how attracted to your date you might be, it’s a mistake to be intimate too soon. This danger is fairly clear: You are engaging in a private, intimate act with a stranger, and afterward it is very hard not to feel anxious and uncomfortable. This can be just as true for men as it is for women; indeed, it is often the reason men back off after an overly early sexual encounter. They think they want sex right away, but it’s no good for men, either.


If you are just re-entering the dating world after a long hiatus, you will already be plenty anxious about this issue. Many women are embarrassed by the changes their bodies have gone through since they were last on the market, and are self-conscious and worried that they are no longer desirable. This is understandable, but not unconquerable. Do what you can to buck up your confidence (if a manicure or haircut usually makes you feel pretty, by all means do it). Most important, though, is to understand that the men you are meeting feel much the same as you do. And since they have advertised to meet a mature women in the first place, they are going to be expecting you to look like Demi Moore, whose sad experience in trying look impossibly fit for her much younger husband turned into a disaster for her.


I am always amused to see the great number of men over 60 who, in their online profiles, describe their bodies are “fit and toned.” Don’t be alarmed (or fooled) by this: It can’t possibly be true. By the same token, if they say they want to meet someone slender, or fit and toned, in most cases that is code for “Don’t be seriously overweight,” not “I won’t see past those 15 pounds you can’t seem to lose anymore.” And, bless their hearts, there are men who say they are interested in women of all body types.


 


Play the Field?


If you are lucky enough to meet someone promising, by all means see him again. But not too soon. This is not playing games, it’s a statement that boundaries should be set up and not crossed too early. Many experts also suggest that, if possible, you date several men at once in the early days, though I have found that some women find this difficult or feel disingenuous if they attempt it. Also, it can prevent you from forming an attachment to someone you really like.


Nevertheless, keep in mind that men often date several women at a time in the early stages, though they may not admit it. And beware especially of the men who want to be with you all the time and seem to adore you instantly. Often they are either neurotic, dependent types, people who are not self-aware, or just plain insincere. A friend of mine encountered this situation. A man she really liked seemed crazy about her in the first two weeks they dated. Then she had to go on a 10-day business trip, but they arranged to meet as soon as possible after she came home. When she returned he had developed “back trouble,” and he kept postponing their reunion. Finally, after stringing her along for two more weeks, he admitted that he had already met someone else, and they too were “very involved.”


 


Red Flags


Though it’s hard, do your best to maintain a balance between open-mindedness and constantly looking for red flags—those irksome signs, big or small, that indicate that a problem is in store. For example: Many women of our generation are offended when a man does not offer to pick up a check. But men have learned to be cautious about this. It is not always a “bad sign,” though of course if you run into a man who invites you out and then expects you to pick up the check—as happened to someone I know (several times!)—head for the hills.


Advanced Dating


As I have said, this process should take a while. At this point, if you meet someone you’d like to see regularly, some of the same issues that have always come up during your past liaisons may arise, and here it is crucial that you don’t repeat pasts mistakes. This can be a problem no matter where you meet your partner, but is nevertheless the single biggest challenge women face when reconnecting with a new man.


 


Next: Dating 505: Making Advances

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  • Jennifer Cheyne March 13, 2012 at 11:09 pm

    Hello! I love this series of articles since I have been (as you point out in your first article) highly ambivalent after my last break-up. But one other issue gets in the way every time I dabble in online dating: telling the other person ‘No Thank You.’ It doesn’t seem to matter how I put it, they always seem offended and/or want more of a reason, etc. (I can’t take any more of those ‘parting shots’ I seem to get, either.)

    If you could give advice on that aspect at some point, it would be great! Thank you!

    Reply