On August 2 I will celebrate my third anniversary as an Evernote user. For the past three years I’ve put just about all of my notes into the fifty-odd “notebooks” in my Evernote database, including the “Alex blog 140” notebook I created to hold my drafts for this series. I use Evernote on my Macbook to draft blog posts or take notes during phone calls; I use Evernote on my iPad to review stored web pages and take notes in meetings; I use Evernote on my iPhone to snap whiteboards and business cards (knowing they’ll become searchable thanks to Evernote’s built-in text recognition). Using Evernote as my all-purpose notetaking, writing and archiving tool, I’ve accumulated a grand total of 3340 notes.

33 months of continuous notetaking in a single application is the social media equivalent of a 25 year marriage. In the three years that I’ve been using Evernote I have tried 711 iPhone and iPad apps, hundreds of social networks and online communities, dozens of project management tools, scores of personal information management tools, and an inestimable number of utilities. A handful have made it into my regular workflow, but nothing has infiltrated my daily workflow as deeply as Evernote.

Just like a marriage, a successful long-term relationship with a web app takes a combination of chemistry, commitment and good luck. If you’ve found an application that you think could be that special something you’ve been looking for, here’s what you need to do to give this new relationship a real chance:

1. Play the field: Whether you’re looking for a contact management tool, a photo editor or an event planning site, don’t jump at the first one you find. If this is a site or piece of software you’re going to use regularly, you want to make sure it’s going to offer what you need. Get to know your options by checking out at least three comparable products before you settle down with the one that seems right for you. I tried a bunch of notetaking tools, and even used Voodoopad for several years, before falling in love with Evernote.
2. Look for long-run potential: Sometimes you’re looking for a little fun; sometimes you are looking for a long-term commitment. If you’re using a new piece of software for something other than a one-off, short-term project, look at its long-run prospects. Does it have a large development team? A significant user base? A deep-pocketed parent company? None of these guarantee a tool will be around forever, but they certainly increase the likelihood that the software you choose will be maintained and ideally extended in the years ahead.
3. Make a prenup: In the haze of newfound passion, it can be tough to remember that even the best relationships may only last for so long. If you’re choosing a piece of software that will house data you need in the long run — whether it’s your contact list, your music library or your email history — make sure you have options if the relationship doesn’t work out. Choose software that stores data in standard file formats, or that offers robust export tools in case you decide to move on.
4. Be monogamous: You’re not going to fall in love with Evernote if you’re still taking half your notes in Word: what makes Evernote work is knowing it’s got everything you want in one place. The same is true for everything from bookmarking to photo storage to online document collaboration. Find your best match, and then commit to it wholeheartedly.
5. Don’t look for everything in one place: The flip side of monogamy is that your happy software relationship can be destroyed by excessive expectations. Even the happiest wife has certain conversations she just has to have with her oldest friend (and not her spouse) and the happiest husband may still have hobbies he enjoys most when shared with a buddy. Don’t expect more from a single software tool than you’d expect from your mate: make room for complementary relationships. Evernote is a great notetaking tool but it’s not your best contact management tool or the right piece of software for live collaborative notetaking.
6. Invest in your relationship: My affection for Evernote has continued to grow because I continue to find new ways to use it. When I incorporated the web clipper into my travel planning workflow, I found that Evernote was the perfect way to build my own travel guide to Paris — one I could then access on my iPhone. When I discovered Everpress for WordPress, I found a new, even easier way of uploading draft blog posts directly to WordPress. Lesson: Just because your favorite tool is working fine doesn’t mean it can’t do even better. Take the time to look for new ways to use or extend it.
7. Embrace PDAs: You’re more likely to love your favorite software tool if it works on more than one device — not just your laptop, but your smartphone; not just your desktop, but your Personal Digital Assistant (PDA). And you’ll find that your love expands still further when you give it a little oxygen: with public displays of affection in which you hold forth about all the reasons this is The Greatest Piece of Software The World Has Ever Known. In proclaiming your love, you’ll deepen your commitment — and may find yourself answering questions that help you discover new tricks or use cases.
8. Work through your issues: Nobody is perfect — nor is any one piece of software. If you’re making regular use of a software tool, you’ll likely find the occasional bug, missing feature or usability glitch. Don’t give up on the relationship! Let the developer or support team know about your issue or suggestion. I’ve had email, forum or twitter exchanges with the dev teams of just about every software tool I use regularly.
9. Show you care: Your relationship with a favorite software tool will flourish when you make a point of regularly showing your affection. You’ll inspire the developers, and help to grow the community of users that helps ensure the future of your favorite beloved or application. So tweet, like and blog about your top software picks…and don’t overlook the possibility of the occasional personal, heartfelt email.