Skip to Content

Taking a Summer Getaway to the Hamps, Fire Island, Nantucket or Another Summer Haven? When is the Right Time to Bring Your Date Along?


Pre July 4th, we thought it would be helpful to give our thoughts and advice on this timely dating issue – when is the right time to go away with someone you are dating?

While there is no magic formula or number of weeks or dates before you can go away together, we believe that if you are not hanging out a few times a week, an invitation for a weekend getaway may be premature and could scare off the person you are dating.

Similarly, if you are hanging out regularly but haven’t moved on to the overnights yet or if you haven’t yet crossed the intimacy line, broach the topic carefully.  Sleepovers clearly suggest intimacy, so if you aren’t there yet, it might be too soon for a vacation. But if you are already staying at his or her place and/or he/she is staying at your pad, ask your love interest if he or she has any plans for summer travel and see where the conversation goes.  If you are heading towards a serious relationship, a weekend away can take it to the next level and cement the two of you as a couple.

Remember that finding love is about taking risks.  If you have been spending some quality time together, consider taking the risk and asking your mate to take a weekend getaway from the hot summer in Manhattan.  It could be the step you need to send you sailing off into relationship bliss.

Of course, there is one clear exception!  If your weekend get-away is a family retreat, you should be more than casually dating before you introduce your love interest to your family on a weekend vacation!  Running into your mom making coffee in the morning might be a bit much for a budding romance.