When you should exchange holiday gifts in a new relationship and what to get them, according to experts

Navigating the early stages of a new relationship can be hard on its own, as it often requires balancing the line between interested and aloof.

It can be even more daunting when it coincides with the holiday season, when deciding whether a gift is appropriate and expected, or could scare someone away, becomes a milestone worthy of its own consideration.

To find out when it’s appropriate to purchase a gift in a relationship, and what types of presents are suitable for these potential partners, we spoke with two relationship experts, Susan Winter, a New York City dating coach professional and bestselling author, and Relationship Hero’s coach Shoya, who presented us with their dating rules for the holidays.

As it turns out, there is such a thing as too early in a relationship for gift-giving, with Winter explaining that “measuring appropriate gift-giving requires evaluating where you are in your relationship”.

According to Winter, the task can understandably be intimidating because the “underlying fear is that our gift will either be too much or too little”.

“We’ll either overwhelm our partner and scare them off, or disappoint them and lose interest,” she acknowledged. “We don’t want to inflate our relationship status, but we certainly don’t want to minimise something that’s going well.”

When it comes to deciding whether a relationship has reached the point of gift-giving or not, Winter said that “discernment is key”.

“Ask yourself: ‘Does this person like me? Do I feel comfortable in this person’s presence? Is what we share mutual?’ A ‘yes’ answer to these questions is ideal,” she explained.

However, if you’re not sure, she says it is best to proceed with caution, as “your generosity won’t increase their desire (only their guilt)”. “There’s no buying your way into someone’s heart. So it’s got to feel real and reciprocal,” she said.

To successfully navigate the relationship milestone, Winter suggests covering your bases by “getting your new partner something,” whether it is a card or a small well-thought-out gift such as a book they’d like.

If you’ve only been on a few dates, Winter recommends giving your new beau a small token such as a gift card to Starbucks or their favourite coffee shop and keeping the denomination small. “$25 to $40 is enough of a leap if you’re just beginning to see each other,” she explained.

According to Shoya, if gut instinct isn’t enough to help you determine where your relationship lies, daters can also rely on more clearly defined guidelines, as she told us that the “too soon” timeline refers to three dates or less - even if these dates took place in December or in the lead-up to the holidays.

“If you’ve been on three dates or less - even if it’s in December and before Christmas - then gifts are not necessary and may also unintentionally send the wrong signal or can overwhelm some people,” she said, adding that a “simple” message wishing them a happy holiday is “sufficient”.

However, Shoya did note that there are exceptions to this rule, such as in the instance you have been invited to “the friends/family gathering, to which a small ‘token of gratitude,’ no more than $20-$30 could be acceptable”.

For couples who have been seeing one another for a month or longer, Winter suggests still sticking with gifts in the smaller range, but opting for something “specific”.

Examples she recommended include a “distinctive card,” or one that is handmade, as well as activity gifts such as movie or museum tickets, or a subscription to their favourite magazine.

According to Winter, these types of gifts are what she calls an “acknowledgement gift”, with the relationship expert explaining that an acknowledgement gift comes with the message: “You’re important and I want you to be happy doing something you love”.

Ultimately, Winter told us that the gift should show that you pay attention to the interests of the person you are dating.

Shoya agreed, noting the guideline is especially useful if the relationship is still in unofficial-official limbo - at which point she recommends spending no more than $50 on a gift.

While a small present is likely fine, Shoya advised against purchasing anything that is “expensive or overly sentimental” and instead looking for something that sends the message: “I thought about you and wanted you to know”.

However, if you’ve had the conversation about where your relationship stands, the gift, while still casual, can lean slightly more sentimental, according to Shoya.

“Keep in mind that if dating gifts say ‘I thought about you and it’s the thought that counts’ then new relationship gifts should say ‘I think about you often and not only do I appreciate you, I’m looking forward to the near future,’” she explained.

If you’re still unsure about what to get, or feel weird spending money on someone who you’ve only just met, non-tangible gifts, such as a nice dinner out, a hike and a planned picnic, a couple’s cooking class or museum visit, are also an excellent option.

According to Winter, who told us that she loves these types of gifts, experiential presents come in handy as they provide an opportunity to make memories.

“I think this type of gift can be more powerful than physical gifts because it creates long-lasting memories,” Winter noted. “Though a physical gift is a tangible marker of someone’s affection, an experiential gift is a shared memory.”

Ultimately, if you do decide you are in a position where you are comfortable giving a holiday gift to new partner, it should convey that you’ve paid attention to what they like and dislike and that you’ve enjoyed spending time together - however brief the time may be.