In the Dating World, Which is Worse: "Divorced" or "Single and Never Married"?

I used to fear that my “Divorced” label would make people – especially potential suitors – judge me. Commitment issues. Baggage. Damaged goods.

Recently I have been wondering about the implications of the “Single and Never Married” label. Commitment issues? Baggage? Unemotional psycho?

Yes. This. Always!
...but, can you be too single? 

This is weighing on my mind because of the new guy I’m seeing. Here’s the scoop.

I met Ryan in early November at a happy hour with a mutual friend. He was in town making final arrangements for his cross-country move back to Ford. (We had actually lived in Ford at the same time several years ago.) We hit it off so he got my number. Over the next three or four weeks while he packed up his life out West, we texted a little, and then more and more. By the time he arrived back in Ford in early December, we were in contact daily.

A few days after his return, Ryan and I met for drinks; he was cuter than I remembered. Yes! Next date was dinner, complete with him picking me up, opening the car door for me, and ordering for both of us. For our next date, he came over for takeout and a movie, which obviously led to some making out. He CALLED ME (did you know that people still do that?) on Christmas Day, just to wish me a merry Christmas. We have hung out several more times – including New Year’s Eve and my small post-birthday gathering.

Sidenote: I’m 35 now. A grownup in her mid-30s. WTF. Moving on!

Ryan meets all four of the basic criteria for dating me:

1. He is college educated.
2. He makes as much or more money than I do. 
3. He’s nine years older than me.
4. He lives alone.

But there's more!

Conversation is natural and genuine. He likes to write!! He is totally a grownup with a real job and a nice apartment but he also likes to smoke a little weed here and there. (This combination is hard to find and I'm a huge fan.) I like how he dresses and he wears cool glasses. He remembers everything I say, including dumb shit like my love for The Bachelorette. He gets along well with his family, including his sisters. The physical chemistry is hot; I know this is important to anyone, but it’s crucial for me to uncover as soon as possible based on the demise of my marriage.

Yes, so far, things are pretty… normal, and I mean that in the very best way! Things with Ryan are just relaxed and enjoyable. I must say, it’s exciting and fun and scary to actually like a guy again. I’m not seeing anyone else. Last time this happened was with Aaron a year ago!

But here’s the thing you guys… Ryan is 44-years-old and has the Single and Never Married label. It seems he hasn’t even had a big relationship! Fair or not, his lack of relationship history raises eyebrows.

Could this be why a person is perpetually single?

Part of me finds his lack of relationship experience very appealing. We are on the same page that being single is not bad – in fact, it can be terrific if you’re at peace with your life and choices. I like that he isn’t one of those people who needs to be in a relationship just to be in a relationship. (After all, I have only really had two boyfriends in my life: the guy I lost my virginity to in 1998 and then my ex-husband, who I started dating in 2005.) Presumably, Ryan has less baggage so there are fewer ghosts of ex-girlfriends for me to battle.

On the other hand, I find his lack of relationship experience a little disconcerting. I’m all for being independent and not “needing” a relationship, but what about choosing to be brave enough to have your heart open? What about experiencing the terrifying thrill of being vulnerable to the person you love? Does he know what it’s like to have sex with someone you love so much that you feel like you could just burst? Does he know how to stay by a woman's side for more than a couple of weeks or months?

Then, I think of my ex-husband, who might be in the dating world. Max is attractive, smart, has a real job, and, OK, he has the Divorced label. Otherwise, he seems like quite a catch. Max is a catch… if you aren’t into physical or emotional intimacy. 

Superficially speaking, Max could seem like a better potential boyfriend than Ryan, but you and I both know how very wrong Max ended up being for me.

What do you think, dear reader? Is assuming commitment or other dating issues from the Single and Never Married person any more justified than from the Divorced person?

Is it a red flag for a person to be in his or her 40s (or whatever age you pick) with no real relationship experience? Would you assume the person is weird/overly picky/commitment phobic? 

Or would you view the person as a sort of clean slate, free of the messiness of past love and heartache and patient enough to wait for the real deal?