By: Andrea Syrtash, Host of "On Dating"

I once received a pretty white gold bracelet from a guy I had gone out with for a few weeks. I didn’t like it – not because I didn’t like the piece of jewelry, but because I didn’t know if I liked the guy giving it to me. I wondered why he felt the need to show me his interest with such an expensive gesture, and it made me question his judgment. I appreciated his generosity, but the fancy gift put unnecessary pressure onto the getting-to-know-you phase that we should have been enjoying at the start of dating. (For those of you who are wondering – no, I didn’t keep the jewelry!)

The reality is that it is not always the thought that counts when you share a gift with someone you are dating. And while I don't believe there are hard and fast rules in dating, I do believe there are smart strategies. It is important to remember that most communication is based on non-verbal exchanges. For this reason, we have to think about the messages we are sending with the gifts we give (or don't give, as the case may be).

Now that the holiday season is upon us, a number of singles are wondering about the kind of presents that are appropriate to share early in the courtship process. After all, at this stage, there is a fine line between sweet and…creepy.

Early into a relationship (during the first 3 months), gifts should be thoughtful but simple. A bouquet of pretty flowers, a book on subject matter that is of interest to the woman you are dating, or a great box of chocolates is appreciated by most women I have interviewed. Treating your date to a fun and interesting activity or taking her to an entertaining show or event also ranks highly. One woman I interviewed remarked, “I love old fashioned gifts like chocolates. You may think it’s boring – but most gals like it, and anything much more seems like you’re trying too hard….”

The problem with lavish gifts too soon is that you are setting a standard that may be difficult to keep and also, you may appear to be too eager. Sure, we want to know that you like us (and don't believe the hype that women want to date jerks!) - but we still want some mystery during the courtship process and time to figure out if we want to pursue a relationship.

After the initial honeymoon period, when you have been dating for 6 months or more, women I spoke to expect more substantial gifts that are based on your knowledge of what they appreciate. My friend's boyfriend got her a massage with a note that read, "You're working too hard! Take a day for yourself on me". She still talks about it years later.

Another woman I interviewed explained that she lost interest in her last boyfriend when she realized he never put any thought into the gifts he gave her. She said, “I had been with my ex for about 8 months and he still didn’t put in any effort when my birthday or Christmas came. He knew those occasions were important to me and I would’ve been happy with anything that showed he cared; but he shrugged and told me he didn’t care much about stupid holidays. It became obvious that he’d always put his interests ahead of mine…”

When you have been dating for a significant amount of time, make your gifts significant. At this point, you know your girlfriend’s hobbies, values and interests. Your girlfriend is expecting you to spend a little more money and a lot more time picking out something she will enjoy.

The good news is that most women I spoke to admit that kindness and generosity are displayed in the simplest of gestures - making sure she gets home okay, being a good listener or sharing a gift that is based on your knowledge of who she is. Those things go farther than a fancy white gold bracelet any day.

Andrea Syrtash is a dating expert, life coach, author and host of 'ON Dating', produced by NBC Digital Studios. Her third book, "He's Just Not Your Type (and that's a good thing)" will be published by Rodale in April 2010. Andrea has made Google 'hot trends’, ranking in the top 100 things googled on particular days between 2007-2009. She has no idea how that happened, but appreciates the (very postmodern) honor. For more visit www.andreasyrtash.com