I don't think I would bring up the issue at all, either via text or on a first or second date/meeting. It's generally not a good way to begin a relationship (whether platonic or romantic) by talking about the things that bother you, before you've even met! You're thinking about this as though this is a serious relationship, before any relationship has even begun. When you first meet someone from a dating site, you just want to hang out with someone face to face to see if you can have a good time together. Can they make you laugh? Are they cute? Do they make you smile? On a first meeting, you're just trying to find out if you click enough to finish your whole cup of coffee-- let alone a second date. Bringing up issues right away is a big turn off, and probably enough to make her decide she'd rather not bother getting to know you. If you're taking things so seriously and making things so complicated this early on, it's probably a sign to her that being around you isn't fun-- there's too much work and analysis involved. If you aren't laughing and having fun, then things like age gaps don't matter. The problem is that you aren't having fun. Take it from a woman who is 28 and went on several okcupid dates back in May and June. If my date brought up their insecurities or what they thought might be issues down the line in our relationship, I would RUN. In fact, I did run. A few times. (i.e. finish my coffee and leave within 40 minutes) If my date doesn't think they are good enough or old enough or educated enough for me, then that tells me they lack confidence, they are unhappy with their life, and I don't want to waste my time on them. If they don't think they're a catch, why would I? Going on a first date is about putting your best foot forward. You don't want to be dishonest by any means, but you don't need to tell your date all of your dirty laundry-- otherwise, she's going to be scared of what is waiting for her when you stop being on your best behavior! Of course, we all have our insecurities and our quirks and our downsides. But, you have to give a woman a reason to like you and enjoy your company--- so that, later on, she will be willing to accept those downsides if, by chance, you do form a relationship. (Which is a huge IF given the ways of online dating). It's just common sense that someone isn't going to accept the worst parts of you unless they get a taste of your best parts, too. They have to balance each other out. So, go have fun, be lighthearted, laugh, talk-- if you click, after a few dates/hang outs, THEN if you still feel like the "gap" is a problem, bring it up at that point. Don't shoot yourself in the foot before you even get to spend time with this woman. Don't get too ahead of yourself thinking about the age/education gap unless there is actually a relationship there to consider. Until a few dates in, you guys are just strangers with computers.

When you're doing online dating, the vast majority of the women you will talk to will NEVER meet you in person. Of those that you have one date with, the vast majority will never go on a second date with you. After maybe 5-10 dates, then you can start to think about what issues you may or may not have if you proceed into a relationship. Spending the amount of time you are thinking about this girl is really pretty counterproductive. It simply doesn't make a lot of sense, given that you don't even know the girl. She's not spending this much time thinking about you (and the several other men she is probably talking to/ going on dates with). Personally, when I was doing okcupid I spent very little time thinking about anyone I was talking to until AFTER a successful first date.