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Ask The Expert: Are You Ready To Travel With A New Partner?

Explore the pros and cons of taking a vacay with your new squeeze.


Dear Carol,

I have just begun a new relationship with a woman I am head over heels in lust with. She is beautiful, sexy, fun and full of life. However, we have only been on four dates. She has invited me on a romantic weekend away for Valentine’s Day. How do you know when soon is too soon to travel with a partner?




Dear Tempted,

You can never really know when soon is too soon! There are many pros and cons of taking a romantic weekend away early on in the relationship. It is a great way to know if you will get along with your partner and how they deal with the stress of potential flight delays, problems with luggage and the hotel not being exactly what you expected.  Sharing a space together is a good way to take a look into the crystal ball of how you will get along living together in the future. All this togetherness is a sure way to find out if you are compatible or not. If you decide to go through with this make sure you are comfortable enough with her to spend 3 days alone with her. Do not take a trip longer than 3 days as if it does not work out it will be short and sweet. Make sure your expectations match up and your idea of a holiday is similar. If you enjoy lounging by a pool make sure she can wind down and share a drink by the pool with you. Plan a mini adventure it is always good to have a day trip planned to take the focus off the two of you. If worse comes to worse always have an exit plan. Can you catch a flight out a day earlier? Is there a hotel close by you can check into? Make the best of it and I am sure it will be the beginning of many romantic holidays. Happy travels!



For more information on Bespoke Matchmaking and to learn about our matchmaking service please click to visit our website

Carol Sugar-Burke is an Executive Matchmaker for NY’s premier gay and lesbian matchmaking service Bespoke Matchmaking.

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