One of our clients recently wrote to our matchmaking agency in a complete panic: he had been on two dates with the woman of his dreams. She was smart, shared his passion for business and the two of them even supported the same charities. They had been at the same fundraiser the year prior and didn’t even realize it! The problem came when his date mentioned that her birthday was coming up – that weekend. Our client wanted to know whether it was appropriate to get his date a gift this early in the relationship and, if so, how to get her something meaningful without scaring her away.

Our answer to this gentleman was a resounding “yes,” and his matchmaker helped guide him toward a beautiful bouquet of lilies (her favorites) that was both thoughtful and personal. She loved them and from what we hear, these two are still going strong.

This client is not alone when it comes to confusion about gift-giving. This is a tough subject at any stage of a relationship. We always tell clients to consider the personal interests your date has already expressed to avoid choosing a generic “man” or “woman” gift. Bath salts and grilling tools are nice, but they really don’t encompass the things you love about your significant other. The key is to get something you are excited for your date to open – not something that looks like it was purchased out of obligation. Our matchmakers have the right gift suggestions so you can express your affection appropriately – whether a holiday comes up after your first date or your fiftieth.

Dates 1 – 2: Gifts are not expected at this point, but if you do choose to surprise your date with a little something, make it inexpensive and personal. If you discover mid-meal that this is actually your date’s birthday dinner, wish them a happy birthday as you pay the bill and, if things went well, go out for dessert afterward. Your date will appreciate the kind gesture.

Date 3: At this point you probably know whether or not you would like to keep seeing your date. By the third date, a gift to celebrate a birthday or holiday is nice, but certainly not expected. We recommend something simple, like a bouquet of flowers or a box of chocolates in your date’s favorite flavors. This is a thoughtful gesture and will keep your date thinking about you as they enjoy their treat at home.

Date 4: The fourth date is a great chance to do something interactive together. Go to the fair or to a holiday market where there is lots to see and do. The excitement will make for a great date and you can buy a small trinket while you’re there. The gift will become a reminder of the fun you two had that day.

Date 5 & up (aka “The In-Between”): There is a magical space our matchmakers sometimes refer to as the “in-between.” This is because you aren’t really a new couple, but you also aren’t ready to think about marriage or meeting each other’s families – yet. Try to think about your partner in terms of their daily routines. Do they go jogging or work out at the gym every morning? Workout accessories might be just the thing for them. Do they enjoy cooking and baking at home? Get them new utensils with a few of your own favorite recipes to customize the gift. If your date has a greenhouse attached to their home, a rare and exotic plant could be the perfect way to win them over. At this stage in your relationship, gifts should be thoughtful and personal. It’s okay to splurge a little. After all, this person could become your best friend and lifelong partner.

Engaged: At this stage in your relationship, you are focused on having experiences together in preparation for your whole new life as husband and wife. Opt for tickets to a show or sporting event your partner wants to see, even (and especially) if it isn’t something you would choose to do on your own. Your partner will appreciate the effort and you will both enjoy memories that last for years to come.

With a little thought and a whole lot of love, you can come up with just the right gift for your partner just in time for the next special event. For more personalized advice, see our holiday gift guide for new couples or contact Kelleher International to find a date worth buying gifts for.