Planning for Your Anniversary …and Other Important Dates

Published on Author GG RayLeave a comment


When you are in a serious relationship, there are only two ways to do things – the right way, and the ‘what were you thinking?’ way. In either case, your significant other will remember what you did forever, even long after you have stopped dating her. Women have the uncanny ability to never forget what their man has done for them. And they universally love to pull the memory of an event out of their archive when it best suits their purpose.

So, if you want to avoid having the ‘fishing trip anniversary’ hang over your head for 30 years, then you need to plan a little better for you important relationship milestones. This article will give you some pointers on what to do, when to do it, and ways to make each important date become more unforgettable than the last (in a good way).

What is a relationship milestone? Since no two women are alike, you need to understand the one you are with before you can honestly say which milestones are important. Some guys like to use overkill and make every week or month of a new relationship an anniversary, but why water down a special event?

If you are dating, most couples would see hitting the one year mark as a major milestone. However, this doesn’t necessarily mean one year from the first time you had sex. In fact, you will impress her a lot more if you choose the day you first fell in love with her, or saw her face in a crowd.

By separating the act of conjugation from your anniversary, you will come across as a sensitive guy. Remember – she doesn’t need a reminder each year about how she got drunk at a club and had sex with you in the washroom.


  • Coming up with the important dates & milestones together.
  • Attach romantic events to your milestones.
  • Remembering them each year.


  • Being indifferent to relationship milestones.
  • Overkill or under-kill.
  • Any comparison you give to previous relationships.

What are the important dates to remember?

There are some women (and men) who are really, really, REALLY in love. In order for them to be truly happy, they need to have about 25 anniversary or ‘special’ dates each year – the first time they kissed, the first time they went to a movie, the first time she had an orgasm, etc. But for the rest of the human race – those of who don’t need the constant Hollywood style love – there are a few key events to do up right. Learn how to plan for the big three: anniversary – wedding or the day you started dating; Valentines Day – how to ‘uncheese’ what should be a romantic day; and, of course, her birthday.


Your anniversary is important for several reasons. First, it is a major milestone in your relationship – every year, not just the first one. Second, you have demonstrated what every mature adult should, at some point, demonstrate – commitment. Third, the world is watching! Well, not the whole world, but her family friends certainly are. This means she will be obligated to tell those people what you did, so it can’t be boring or crappy. Fourth, you can make up for a lot of bad things you did over the year, if you do the anniversary right.

An anniversary – particularly the first, tenth, 25th, 30th, 40th and 50th, are important ones. So think low-key and sexy, like a cozy ski lodge or cabin. It should be about the two of you, definitely not a group date.

Planning Tips

Get her involved

  • If you are a bad planner or lack the romance gene, get her involved in the process. That way she will be as much to blame as you, if the anniversary is lousy.

Plan ahead

  • Last minute plans can be fabulous or horrible, but they typically turn out bad due to a lack of availability.

Be creative!

  • Anyone can go to Niagara Falls, but not everyone goes over it in a barrel.

Surprise her

  • Keeping her in the dark is another way to hype things up, so beware of her sneaky uncovering ways!


  • Nothing will make her feel more young and sexy than a trip into the past. Try and recreate a special event, like the first time you met or kissed.

Valentine’s Day

We all know how overdone Valentine’s Day has become, but it is still considered a romantic day. This means there is an expectation for you to do something romantic. When she is at work the next day, you don’t want her to be the one who didn’t get anything. So even if she doesn’t want to go anywhere special, do something small anyway.

Planning Tips

Avoid the cheese factor!

  • Although it might be tempting to dress up as cupid and shoot her with a rubber arrow, she might be embarrassed. And you can forget going out for heart-shaped food (pizza, cheesecake, etc…) – try not to go ‘Hallmark’ on your lady!

Make her feel sexy!

  • Valentine’s Day should be romantic, so don’t buy her anything practical. This means you buy red roses, candy, sexy lingerie, and sex toys – but only if she is into it and won’t be offended.

Avoid other couples!

  • Group dates on Valentine’s Day? Not a chance! This is supposed to be the day when you can express your love (and lust!) for each other. Focus on her and only her.

Her Birthday

One sure-fire way to damage any relationship is to forget her birthday. Remember how excited you were as a kid when you got to be king for a day? Parties, presents, food, cake, and being the center of attention – that’s what birthday parties are all about. Just because you are adults now is no excuse to change things. But now you have to make a choice between the intimate birthday for two, and the large party with her friends and/or family. You should already have an idea on what your partner would prefer, or you could mix it up from year to year.

Planning Tips

Surprise Party

  • These are great because they show you care enough to plan well in advance. However, avoid overkill. Only have one or two of these in her lifetime.


  • Always start it at your place, as in having friends over for dinner, drinks and gifts. She might feel awkward if she has to open gifts in public.

The Present

  • Please use your brain. Nothing practical, and it has to have meaning. If you bought it at the last minute, it will show.

The Card

  • Because it is as important as the gift, you should have an eye out for thoughtful cards 12 months of the year. Avoid cornball stuff. Go for simplicity and something meaningful written by you. Blank cards are best because you can write exactly how YOU feel. Not what someone else’s idea of a sentiment is.

Final Thoughts

If you plan right, you will never have an unhappy woman on your hands. And keep in mind that there are going to be at least two of you at these important events, so if you make her happy, you will be even happier. Just make sure you don’t set the bar too high too quickly, otherwise you will eventually hit the wall. Always make sure you leave room for improvement each year, so your relationship will never grow stale.

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