The Summer Getaway

Walking outside on the concrete city sidewalks on perfect summer days like yesterday, you can’t help but daydream about all of the wonderful things you could be doing by the ocean or in the mountains … Not to worry, the weekend is just a few days away and the relaxation (or adventure) can begin. If you’re single with no particular love interest in your life, it’s simple – you’ll gather your typical partners in crime and go to where the guys and the girls are. If you’re in a relationship, it’s also easy - you can rebook that romantic bed and breakfast you stayed at last summer. Done.

But for those individuals who are in that no man’s land – somewhere between a first date and enough dates to know each other’s annoying habits but still like that person anyway – the prospect of inviting this new spirit to share in your wanderlust is fraught with both excitement and concern. Suddenly, images of frolicking in the ocean and outdoor tiki torch lit dinners give way to myriad complicated questions:

• Is it too soon to spend the whole weekend away with this person?
• What does it mean that he asked me to go away?
• What, if anything, will she read into this invitation?
• What if things go terribly wrong and I can’t stand this person’s face by day two?
• What if things go well – am I prepared to have sex with this person? Am I prepared to be exclusive with this person?
• Who pays for what? If I am the invitee do I have to pay for anything at all?

Tough questions, and obviously, the answers can vary depending on the circumstances.[1] Too bad there isn’t a guidebook that, in addition to walking you through your various hotel and restaurant options, asks you: are you really ready to take this trip? Please answer this five page questionnaire before you book. You can thank us later.

Nevertheless, in an effort to shed some light on these questions, let’s start with the request to go away for the weekend – what does it mean? Under most circumstances, it is usually the guy initiating the request for a weekend trip and so I am going to work with that “sexist” assumption for purposes of this blog. Ladies, you might be inclined to think that if a guy is asking you to take a weekend jaunt with him it is a promising sign of his level of interest … but be very careful before you read too much into it as that isn’t always the case.

The new man in your life may have a pattern of asking women he is just starting to date to go away with him (this is particulary likely to be true if he has a vacation house at the proposed destination). He may just have a strong desire to get away and doesn’t want to go by himself. And, of course, he may just simply want to get laid. But please don’t take me for a Debbie Downer - sometimes a man’s request to take you on a weekend getaway can be a very good indication of his level of interest and so the excitement with which you share the news with your friends will be entirely justified.[2]

Accepting the request to go away. So, you’re inclined to accept because you are comfortable in the connection you two have and believe that his intentions are good. Still, you should ask yourself "do I know this person well enough to be stuck playing house with him for a few days?" A friend of mine recently went on a date in the city with a guy who has a house in the Hamptons and they had a great time. After their first date, he invited her out east. She debated about going but ultimately accepted because the weekend sounded so appealing (perfect weather, tennis, lots of great meals). After 24 hours, she was texting me how she could not wait for the weekend to be over. As she recounted after, it was painful.

Lesson to be learned: going away before you’ve had at least several good dates and at least a sleepover or two is probably not a good idea. As a rough rule of thumb, you’re probably safe going away after five or six dates. By then, you hopefully know the person well enough to feel comfortable with him or her and you can feel relatively assured that there is not going to be some type of Dr. Jekyll/Mr. Hyde transformation.

Another cause for pause for the women could be a strong desire to go away countered by a fear of rushing things in the beginning and potentially jeopardizing the longevity of the relationship. This is a valid concern and can be a tough call. When you first start dating someone there is a sense of mystery about the other person – you know very little about this new object of your affection and the tiny tidbits of information you get on each date are rewarding and intriguing. However, after four hours (each way) in the car singing 80s music off key together, hearing about each other’s childhoods or relationship war stories (coupled with the 24/7 time together away), sharing a bathroom together, waking up sans make up, with matted hair and morning breath it is inevitable that some of that “new mystery feeling” is going to be gone. In addition, you’re not going through the exciting process of “scheduling” time together because, well, you’re together all day long … You’ve jumped a whole level in the dating game that can never be regained. Something to take into consideration.

Of course, there is the upside. Should you have a great weekend away together, you will have started off your relationship creating some wonderful memories. Instead of meeting for drinks or dinner, you are experiencing something fresh and new together which is always welcome after you’ve been on countless dinner dates. Naturally, you will likely get to know this person on many more levels now that you are away from the stress of work and our demanding city life. And, of course, seeing that you can enjoy each other’s company for hours on end is extremely valuable. The pros are looking good so you go…

Ok, now you’re having a phenomenal time which leads to the sex question. We all know that the weekend away expedites the question of when sex enters the picture. Are you booking two rooms or one? Are you sleeping in the same bed? (Ladies, the guy’s assumption is going to be that you are staying in the same bed unless you disabuse him of that notion. If you have an issue with this, you definitely want to iron these questions out before you hop into the car or train). From the men I’ve spoken to, the vast majority believe that it’s almost a foregone conclusion that if you’re planning a weekend trip together there’s going to be sex. Women, you might be on exactly the same page or not, but you need to be aware of this.

Then there is the question of who pays. Guys, if you’re asking a girl away for the weekend, it’s fair to assume you have at least all major expenses covered (lodging, rental car, dinners). But, Ladies, this doesn’t mean you should look at the weekend as an all expenses included trip allowing you to leave your wallet at home. The one thing many of the men I speak to state they can’t stand is a woman who won’t open her purse on a trip to even purchase her own pack of gum. At a minimum, you can’t go wrong at least offering to pick up a lunch or dinner. If the guy is dripping in money, it’s my opinion he absolutely should not accept the offer, but otherwise, a more normal guy will likely appreciate the effort to contribute a little. Certainly, one of the most important travel tips I can give is to show appreciation. Someone just took the time to plan a nice trip and spend money on a weekend away for the two of you. Saying thank you at the end of the weekend with a nice note or home cooked meal can go a long way.

And the million dollar question: What does this weekend retreat mean for the relationship? Potentially nothing. Potentially everything. Guys, be on notice that what started as an innocent idea for a carefree weekend excursion can lead to serious expectations by the time you’re putting her Louis Vuitton bags back in the trunk on Sunday afternoon. You’ve now (potentially) been intimate - are you exclusive? You just spent a sizable amount of time together - are you going to be talking each day? Seeing each other more frequently? Some women might give the weekend away far more meaning than you do, so if you don’t want to deal with the questions that will inevitably arise once you are back to reality, you may want to postpone your summer get away a few more weeks.

But the good news is that once you have all these vexing questions out of the way, you’re on your way to a weekend of summer lovin.’ Bon Voyage!


[1] Should the potential weekend away involve a wedding or meeting someone’s family members, the decision is even tougher and requires even more deliberation. You are entering a whole new dimension of the weekend getaway conundrum.

[2] But, women, you still have to be wary. Many times when a guy is really into a woman he has just started dating (often pre-sex) he will start planning all sorts of weekend excursions with the most sincere intentions … but there’s no guarantee that he will still feel that way three weeks from now. Also, be suspect of the guy who is insanely into you right away. For example, he’s talking about planning a trip in the Fall (when it’s still May) and you’re not even speaking on a consistent basis.

Why wait until the end of summer to take proactive steps to meet someone wonderful? Now is the perfect time to do something for yourself and potentially be planning a romantic summer getaway of your own! www.sundayatnoon.com