My Obsessive List of Back-to-Dating Questions

After a self-imposed exile (is that the right word?) of dating, I find I want to do it. Uhm, dating, that is, and not Do It…which is an entirely different thing, but yes, something I’d like to do too.

I’m having a little trouble in this area though. Mostly, it’s my brain. It’s getting in the way. At 36 and divorced and a single mom, I have a whole new list of dating questions and I don’t know the answer to them.

Here are a few:

1) Can I blog about a man I’m seeing if he reads my blog? (If I’m seeing you and you’re reading this, you may want to stop. Seriously.) My blog could prove awkward. A girl needs secrets…and while dating you want to appear perfect and like you always smell of scented lotion. You do not want to come off as neurotic, strange, or possibly obsessive…which are all conclusions you could make about me if you read my blog.

2) And if I blog about dating, can I do it while I’m dating or do I have to wait until months later? I keep envisioning me on a date that’s going really well, so well, we’re on some couch somewhere making out like teenagers and I say “Oh! Hold that thought! I want to tell everyone I’m making out like a teenager!” Then I run to the computer, type away, and then run back.

3) Do I wait for a man to approach me and ask me out or embrace newfound Cougar-within and approach him? And what are the new rules? When do I talk about my kids without making it sound like I want a new Daddy. I don’t, but the kids are an essential part of who I am. Like down to the DNA.

And men my age are usually divorced and/or fresh out of relationships or wounded by relationships. Do I wait until they’re more well-adjusted? Is someone who’s bitter about their ex best to be avoided? Or do I just jump in there and say “Hey! I’m here! Let’s do it!” (Dating, again, people. Not Do It. That’s for later.)

4) Can I date someone whose friend I dated but that was like in college when I didn’t know any better? That’s probably asking for a whole lot of drama.

5) Are all my former students who are now in their thirties off limits still? Because role-playing could be fun. No. That’s off the list. If you’re at my school looking to hire me, I would never NEVER date a student. (Again.)

6) Do I immediately mark off the list anyone who is living with their parents. Times are tough. It’s a new era, and lots of people need to get back on their feet.

7) Could I possibly have a fling? One that doesn’t necessarily mean anything? That would be free and easy, wouldn’t it? A passionate fling on a beach somewhere where I have long hair and a bikini body that makes the gods jealous? (Oops. Just slipped into fantasy there.)

8 ) I just answered my own question. I don’t think I’m a fling type of person. My heart always gets in the way.

And most importantly….

9) How do I stop that heart from getting broken? I’m terrified. Absolutely terrified of falling in love with the wrong person. I’m also terrified of falling in love with the right person.

10) I don’t really have a #10 but I felt like I couldn’t end a list on 9.

So that’s my obsessive list for dating. Who knows the answers to these questions? I could ask my therapist, but he’d probably tell me to just trust myself. I’d rather have someone just tell me what to do and not do. It would be a whole lot easier.