Edit: My wife is the cofounder of our life and family together, and I have yet to find a business opportunity that could ever compete with how she makes me feel.
Maintain perspective. Life is short. Maximize for happiness.
Embrace the moment, the chaos, and the loss. It's the human condition.
Like everything else, this kind of relationship has good and bad points.
The best thing was the degree of understanding. I've never been in a relationship with someone with such an incredibly innate understanding of my career. It was truly magical.
But, then there was the bad. Until you've been in this situation, you can't understand how deep the conflict of interest can get. Sometimes, co-founders need to have frank conversations about performance. When you're in a romantic relationship, frank feedback can create deep wounds. Then, in our case, once the magazine died, our relationship died too. The double whammy of a failed startup and failed relationship was unlike any other breakup I've ever experienced.
All that said, I'd do it again in a second. The relationship was so good while it lasted and Stacey is still one of my closest friends.
First, make sure you have clear founder agreements, focusing on the case where one of the founders leaves (this usually implies vesting of some form). If you enter a relationship and then break up, the odds of one of you leaving at some point is increased.
Second, if you have investors, a board, and/or other key stockholders, you should consider disclosing a serious relationship (should it get to that point, for some definition of "serious").
Some will say, "it's none of their business!" but it kind of is. Most companies of any size have a policy on workplace relationships, and the minimum is usually that they must be disclosed. Even if you're too small for an HR department, the issues around potential conflicts are the same.
You never, ever, ever want to be in a situation where you date, break up, one departs, the company is compromised, and an irate investor later says, "you never told me!".
With that said, while I can't speak from experience, if you are equal founders I say go for it. If one of you is in a position of authority over the other it becomes much more tricky.
The only down side I can see is if you two break up and it gets messy. In which case, having a good board of directors that can be neutral and think about what is best for the company is important.
Edit: a little bit from personal experience though. If your startup hits a rough place and you need to sacrifice things like pay, it can be helpful when your significant other has a stable job. And if you both work for the same startup that is not an option. Money is what breaks up most relationships and if there is one thing startups are good at, it is creating money problems.
Overdue bills, not being unable to put food on the table, losing your house, ruining your credit score, not being able to afford your kid's college, not being able to afford medical care, etc.
Not to mention it helps cause or bring out depression. Which is a crippling mental condition that requires a lot of awareness and fortitude on behalf of the people around you (aka your significant other).
The kind of stuff people often commit suicide over. In fact, I'm shocked the suicide rate in startup founder's isn't higher. Never mind the divorce rate.
Now you can argue up and down that "all you need" to whether those things in life and a relationship is "strength." But not everyone can be strong all the time.
And it is even harder to be strong when, for example, one partner is the cause of most of the money troubles and you know leaving them would solve the problem for you. At some point the basic human instinct of self-preservation comes in.
A romantic/sexual fling can end very, very poorly, and such problems can carry over into the startup. Would someone be happy if he felt she used her and then dumped him for the next guy? If a cofounder marries some other guy later, would her husband be happy that she still sees her ex every day at the office?
At least with office romances, someone can change jobs if it gets too awkward.
Yes, it rarely ends well.
If you end up in a long term relationship or even get married, then the boundaries between work and home get blurred, and on top of that, if you have vested interests in the success of your work (which is your company) things could easily get out of control - clashing egos, 1 partner feeling the other is not doing enough at work, or at home, or both.
I've seen 2 of my close friends end up like that. Doesn't mean that's the norm, but things get ugly over a few years...
That doesn't mean you should not pursue the romantic relationship, just saying be cautious and don't over-commit too soon. Wait for the "honeymoon period" of the relationship (if you do end up moving forward) to pass and see how thinks look. In "normal" relationships, this period is usually anywhere from 6 months to a year or two...
To be quite honest, I think it's difficult to avoid getting attracted to your co-founder. You'll be going a lot of places together. I've shared the same hotel & bedroom with my co-founder for months. And you tend to share all secrets together, very much like a married couple, if not more so.
Perhaps it's better to discuss this with the person herself. Work out the best way forward to make it work. Good luck!
Both these things are hard and as such both will have a hard time succeeding but they're both worth the trouble so I say go for it with these considerations:
You need to have an agreement that you will be professionals first while at work and that at work, work comes first. Your company is very important to you and emotions(good and bad) will tend to take precedence but you have to be cognizant of your emotions and try to separate them. You have to.
For this reason, have an agreement of sorts, a kin to a prenuptial agreement. Answer questions like if things go wrong and you can't work together anymore, what happens then? There's a reason companies have strict policy for workplace relationships and how they ought to be handled.
I guess it would be harder to make sure the relationship would stay, but if you don't concern yourself with such things, sure.
This may be a little old-fashioned, but I'd take a serious look at getting married before seriously dating. You already know each other well and trust each other, and it appropriately signals the seriousness with which you're approaching things.