Online Dating: Should I Fly Out To Meet This Person Or What?

If you are involved with online dating at all, you have likely been confronted with the possibility of meeting someone far away. There's something very romantic about this notion, almost (or, um, exactly) reminiscent of Sleepless In Seattle. I mean how killer is it to go half way around the world for the right woman?

Granted. And if it works out, it's amazing. But lets talk for a while about all this. From this conversation I trust you will be able to go into such potential situations armed with more wisdom than ever before.

Before all else, let's discuss how two people get in this situation to begin with. It's no secret that some dating sites have built their software so as to put as many people in touch with each other as possible. If a site is one of the minor players, which translates to fewer subscribers, you are likely to be encouraged to communicate with more people from other states (or countries) than you would at a Match.com or Yahoo Personals. IM "pen pals" come of this, and this is cool, but sooner or later, you are likely to notice--and talk to--someone who amazes you but is either in Alaska or somewhere that may as well be. If you don't want to be tempted by someone on another coast who is giving you warm fuzzies, join a bigger dating site and keep your searches close in proximity.

Now, if you live in a very remote area with a very small dating pool to fish in, this kind of long-distance interaction made possible by the magic of the Internet may flat-out be the best thing that could ever happen to you.

I however, like the vast majority of us in this country, am fortunate enough to live in a major metro area. My thought process has gravitated towards the notion that if I live in a city of over a million people and can't find someone to hang out with here, I need to look in the mirror and consider the problem might be my own. Read that last line again. Does it speak to you?

On the other hand, there is the whole concept of the perfect soul mate. I am on the fence about this one (see future article), but there is no doubt that the possibility exists that your absolute best choice in a long-term mate might not live in your city. I will not discount that.

OK, so if you are going to do this sort of thing, what is there to know?

First, do all the qualifying you can before the meeting. Talk. A lot. Forget the pictures, spring a whole $20 on a web cam and use it. Pictures do not capture mannerisms, etc. like the cam does.

Next, if you are in a remote area and the one you are talking to is in, say, Los Freaking Angeles you have got to ask this person what is driving him/her to look outside a metro area of 12 million people. Do it. And don't accept some Pollyanna answer (e.g. "You are special", "I've been wanting to move to Egypt, ND anyway", etc.). Refer to my previous article titled "Signs Your Date May Be Married" for a refresher course as to other reasons why these conversations are important. Use judgment here. An example of an acceptable answer may come in the form of "I'm a native Texan here in NYC, and I really want to settle down with someone I can relate to better." Take the blinders off and listen during this conversation.

Next, figure out who is going to do the "heavy lifting" as far as travel goes. As chivalrous a man as I consider myself to be, this one should not be automatically shouldered by the guy. Let's use the potential situation in the previous paragraph as an example. If Boy lives in Los Angeles, and Girl lives in Egypt, ND common sense says that the two of you would have a much better chance of having a great weekend together if Girl flies to Boy. As far as the costs of all this, consider who has more resources. If Girl travels on business and has 500K frequent flier miles she'll never get around to using (unless, ironically, she meets the right guy to travel with), then there is no sense in having the guy buy a ticket. You get the idea. I personally believe that when both people have an investment in a weekend like this, both are more committed to its success.

Next, make all the logistical arrangements for the visit, and communicate clearly about it. The one who is flying in should reserve a hotel. This takes a lot of pressure off the situation, which believe me will be a plus. If you two decide to cancel the hotel, that's your own business, but having the option there was good planning nonetheless.

Read the sentence that follows this one twice: If you fly out to meet someone you have never met or barely know, absolutely positively make flight and hotel reservations that have great flexibility. If it costs a reasonable amount more for a fully-refundable reservation, do it. This way if things go awry quickly (or heck, what if the other person flakes out on you completely at the last minute) you are hassled less as a result.

We've all but established that if there are plane tickets involved for a first meeting, you are almost 100% doing this because you are expecting something SPECIAL to happen. People are not flying cross-country for casual flings, and even if they are, what I am about to say still will probably hold true.

OK, so where does the rubber meet the road? Right here: ONLY TWO THINGS CAN HAPPEN when people meet each other like this:

1) "I'm Frustrated!" v1.0 You learned (and typically very quickly) that there was no chemistry in real life. Or worse, the other one did. You feel angry and/or deceived, disappointed, empty, hurt, ripped-off. A lot of time, emotion and $$$ were wrapped up in this, and it didn't go well. I've even heard the tale of someone getting off the plane, meeting the person, and immediately going right back to the check-in counter to change the ticket to the next flight out. That's sure to cause an empty feeling. And what's more, now what are you going to do all weekend?

2) "I'm Frustrated!" v2.0 Unlike casual first dates close to home, these weekend trips are inevitably hyped like mad by both participants. So what if It lives up to it? It's everything you dreamed it would be. Um...Now what? You part ways after Some Enchanted Weekend and you are still 2000 miles away from each other--except now you are obsessed! How often are you reasonably going to get to see each other? And how will you develop this relationship? Who is eventually, and inevitably, going to move? And when the move happens, how do you know that things will still be wonderful when you start spending more casual blocks of time together?

Don't kid yourself. Ending the weekend with a sentiment of, "That was so nice. It was fun to get away and have some fun, and now I've made a nice friend I can reminisce about from time to time and keep talking to as before" is a fairy tale. There is zero chance either person will leave the weekend feeling like that, let alone both. If you disagree, I'm open to your counterpoint, but I do believe this is truth.

Blind optimism translates to being straight-up naive when it comes to this stuff. Always keep that in mind. If you have good stories, hook a brother up and I'll print some of them in the next "Letters" segment.

About the Author

Scot McKay's dating strategies are found at http://www.deservewhatyouwant.com/ . Stop by right now and grab a FREE e-book ($20 value) when you sign up for the X & Y Communications Newsletter, which is always packed with unique and practical dating tips.

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