5 Rules for Bringing a Date Home for the Holidays

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By Richard Craig

bringing date home holidaysOver lunch, I was talking to the editor of this magazine and the holiday questions arose: When you are dating someone, no matter how intimate, what are the pitfalls of bringing the person you are dating home for the holiday(s) with the family?

So, I began asking everyone and the feedback was funny and scary.

No one, and I mean NO ONE, had the same suggestion, but one theme rattled through each response: Be prepared for the unexpected question, and please (their plea not mine) do NOT put your kids in the middle of having to emotionally invest in a relationship you and your date have not thought through. This happens all the time when we rush into introducing that special someone to the family. And, the holidays are ripe with risk.

A dear woman friend of mine carefully orchestrated bringing her new love to the family Thanksgiving dinner. They had no kids, but her mom and dad, great aunt, and the requisite nieces, nephews, brothers and sisters were there. They decided to be cool about the relationship and how serious, or not, it was.


Over dinner the little niece looked at the new boyfriend and said, “Are you gonna marry Aunt Katie?”


The room stood still until the brother-in-law, who drank a few too many glasses of wine said, “No they just sleep together.”


The great aunt piped up, “That’s not moral, you know?”

That is what they call a hat-trick in hockey (three scores in one game). I do not need to tell you how awkward it was. The lesson was clear: Inviting that special someone to the holiday table can be a wild ride.

After a holiday dinner, the guest always, always, always gets a review. Too often the review is a comparison to the last date you invited to dinner. Don’t pretend that does not happen – we all do it.

So, I stopped at Starbucks afterward my meeting with the editor, and my usual crowd of friends were there, so I posed this holiday dinner question. They all groaned while recounting their experiences, but, the advice was boiled down to five points:

1. Never put your kids in an environment of having to support your relationship without careful planning and forethought. If your kids are there and this is the first time they meet the person, there is a lot at risk to everyone. The best option – if you must use the holidays to introduce your lover – is to create short face-to-face meetings a few days before the holidays.

2. If you are going to stay overnight, expect and offer to sleep in separate rooms – avoid the questions.

3. Don’t bring a casual date to a holiday dinner. Bad idea. But if you must bring a casual date, brief the hosts as to the relationship status and ask for their help if things get awkward.

4. Everyone agreed on this: Only invite a date to a holiday dinner if the person is someone with whom you want a long-term relationship.

5. If anyone has a history of drinking and being even a bit out of control, don’t bring a date. However, IF you do, have an exit plan.

Now please send me your ideas, thoughts, and stories. I plan to write a column on what to buy for Christmas based upon how long you have dated.

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Author: Richard Craig

Richard Craig is not my real name, but if asked in public I will not deny who I am. I do write, and have for a long time. I am over 50, single and honestly baffled by the single community in Laguna at times. My job is, with your help, to figure it out.

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  1. Sitting here thinking of the invitations I received and your 4th rule “Only invite a date to a holiday dinner if the person is someone with whom you want a long-term relationship,” I wondered should you also not ACCEPT a holiday dinner invitation if you don’t want a long term relationship?

    What do you say, Richard?

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  2. I love this column, I don’t always agree with it but it is the only place in Laguna that actually talks about single things.

    This column reminded me of the Christmas Dinner where I invited my girlfriend, the arrangements were to be individual rooms, which was fine with us since we had not slept together. Well, my mother was so taken with Karen that she insisted that we share a room (that abutted my parents room and had no private bath). Clearly it was awkward, but the killer was that the family thought I was dating way above my station!!!

    What a twist on a story. But we did marry eventually and to this day my mother introduces her as the daughter I should have been.

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  3. Bringing home dates for holidays it’s a disaster waiting to happen during an uncomfortable situation. It’s always difficult for me, the forced family holidays. Seems like way too much tension surrounding these things. And I think some people get kind of funky around this time year. I know I do.

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  4. Reminds me many years ago when I went to a holiday party and we were going around the table saying the best thing about others at the table. My boyfriend’s 5-year old nephew said, “The best thing about Uncle Danny is that he gets to sleep with Sarah.”

    Inviting someone home for the holidays depends on your family, your date, and the size of the dinner party. There are many variables.

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