Holiday Dating Guide For People In Relationships

Are you dating someone new? 

Have you been dating for a while, but the two of you aren’t exclusive (yet)?

Or, are you now dating exclusively and looking for the edge?

Relationships get tricky during the holidays, so we prepared this Holiday Guide to help you navigate the whitewater rapids of love and arrive at your destination with yourself inside the canoe, paddle intact and hair dry!

It’s strange how you’re suddenly thrown into this gray area of what’s appropriate (or not) during the holidays.

For instance, you may wonder whether the gift you’re giving is too cheap or too expensive, or if it’s too early (or waaay overdue) to meet the parents.

Don’t worry… I got powerful tips for you in this article.

Here are some holiday do’s and don’ts that should help you out tremendously in figuring how to “do it right”, regardless of the stage of your relationship:

If you’re dating for less than one month…

Gift Giving:

Don’t give an expensive gift just yet. It’s too soon to do so because sometimes people f-r-e-a-k out when they receive an expensive gift from a relative “stranger”. An expensive gift may make them wonder about the level of commitment you expect from them in the future.  

What to do instead?

Shoot for small and thoughtful gifts. Just pay attention to simple things they’ve talked to you about before, then find a way to honor their unmet need (or want) with a small gift. It’s just enough to show that you care, but not too much that it sends a red flag.

Meeting the Family:

It’s a bad idea to bring your new fling home for the holidays – no matter how fond you are of him. Give yourself time to feel him out and determine whether it’s going to work out or not before expecting everyone else to embrace and accept him.

What to do instead?

The best thing to do is to keep him from meeting your family completely. However, if you insist, make the situation more casual by meeting a few family members at a café or bar instead of bringing the new guy to a full-fledge family gathering.

Social Settings:

When finding yourself in a social environment together with your new guy, resist the urge to spill everything about your new love interest to everyone at the table.

Instead, simply introduce him to the group by his name and leave it at that. If you go any further by calling him “your friend”, you run the risk of offending the new guy and that’s just make up for a sour night.

Conversely, you run the risk of having a sour night anyway by NOT introducing him as “your friend”, but I’d rather repair this type of situation with a conversation than have my close friends and associates talk behind my back about yet another “friend”.

If you’re dating for months (up to a year), but are not exclusive…

Gift Giving:

It can be tricky buying a gift for someone who you know really well, but aren’t seeing exclusively. You don’t want to create an awkward situation by asking, “Should we get gifts this year?” You also don’t want to show up with a lavish gift, while they are empty handed.

What to do instead?

You can let your non-exclusive partner know that you got him something, but play it down by letting him know that “it’s no big deal”. This way, they don’t feel compelled to having to buy you a big gift.  

Meeting the Family:

If you do invite him over for dinner, don’t get upset if family and friends think the two of you are exclusive. Instead, when someone brings up your relationship in conversation, just let them know that the two of you are there to have a great time and that’s it.

A great idea is to always pre-coordinate your responses beforehand so you and Mister Non-Exclusive present a unified front and avoid having to explain yourselves to your (nosy) family.

Also, it may not be a great idea to invite him over for a big family dinner. Shoot for the smaller, more casual gatherings before bringing him to La Familia.

Social Settings:

If you’re heading out to an office party, do your best not to bash anyone who’d be there to your beau beforehand. Allow him to meet your co-workers and friends unbiased from your comments so he can make his own objective assumptions when he meets them.

You also want to hang a little close to Mister Non-Exclusive and not ignore him in favor of having a conversation with your besties. Just because you know everyone at the party doesn’t mean he does too. Make sure he doesn’t feel alone, forgotten and left with strangers.

If you’re dating exclusively…

Gift Giving:

Congratulations! You made it to Exclusive Land. What now?

It’s actually easier than you think.

When buying gifts, be sure to get something that your partner will like; not just something you want for yourself – meaning: no couple’s massage gift certificates, candles or anything like that. Go for gifts that match what he’s really into.

Meeting the Family:

If you travel to your family home for the holidays, don’t stay there the entire time. It may get a little socially uncomfortable for the both of you after a while because naturally people start proding with questions, the “baby talk” comes out and it’s just not a good situation after a few hours or days.

What to do instead?

Be sure to build in some time to go out and hit up the local bars, free community events and other social activities away from family where you (and now, Mr. Exclusive) can spend time together without family pressures.

If you’re going to his parents’ home, I hate to break it to you, but you’ve got to impress the momma. A great way to do that is by offering to help set the table or clean up the mess afterwards. That’s just how it is 😘.

Social Settings:

When going to holiday gatherings with your partner, consider his feelings.

Monitor his demeanor throughout the party to pick up on non-verbal cues that he’s ready to leave and go home. It’s a guy thing… they just get bored and won’t say anything (at least the ones with decency) because they don’t want to make you feel rushed. 

What’s Next…

You’re now armed with tools for success to make it this holiday season, no matter the stage of your relationship.

Now, get out there and enjoy your time together!

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