What I Learned On 30 First Dates After My Divorce
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By Jennifer, Guest Author - November 21, 2016


Dating different guys helped me create a list of characteristics for what I want, which is a helpful exercise. I’m not married to that list, though. A guy can check all of the boxes, but it comes down to that connection. It’s either there or it isn’t. I also learned my process for dating. 


After my divorce, I had little idea what kind of guy I wanted to end up with. I met my ex-husband when I was 19. Prior to that, I'd only had a handful of relationships, but always had a lot of guy friends.

I decided to be open to dating the whole spectrum: guys from their mid-20s to early-60s with incomes ranging from hourly workers to men with enough personal wealth they don’t ever have to work another day in their life. It spanned professional athletes to desk jockeys. I thought I’d find some commonalities between age groups or income/education levels, but nope. Communications styles, levels of commitment, levels of energy, and the way they treated me all differed. It just boils down to the individual and what type of guy he is.

Buyer Beware of These Guys When Dating After Divorce

The Bench Warmer (still finding myself/still a boy): These guys are the most frustrating because some of them have potential. But if they aren’t going to get off the bench to chase you, you need to move on. They lurk. When you find yourself saying a guy has potential, no matter how many boxes he checks or that feeling you get, you need to move on if he refuses to show his own interest in you. If and when he ever decides to step up to bat, then he can get in the game. Until then, you’re better off alone.

The Emotionally Unavailable: These guys are harder to spot. Sometimes you can get further down the road with someone and realize they are never going to be able to take a relationship to the next level. Something is holding them back. It may be an ex or something else that has happened. My friend got mixed up with someone who was emotionally unavailable. It didn’t stop him from pulling her close and then pushing her away. It’s not a good place to be.

Take a hard look at how you feel around him. Do you mostly feel anxiety or do you know where you stand? Even if there are brief periods of feeling amazing, but most of the time you’re just anxious, then they may be emotionally unavailable.

The Skirt Chaser: These guys are all about the chase. You will never be enough because you aren’t special to them, no one is. They just want a skirt to chase, doesn’t matter which skirt, so long as they are “in the game.” Once they feel they’ve caught you, they don’t know what to do with you and they’re on to the next one. This one is easier to spot quickly, just look at his Facebook friend list. TONS of single women? Yep, red flag.

The funniest example of this was when I went to a work conference. Some mutual friends introduced me to this guy (I’m assuming it was for the sole reason of us both being single, because as soon as he opened his mouth, I was like ‘no’.) He grabbed my phone and put in his number using the nickname “hot pants.” Classy. I bumped into him throughout the conference and he made no effort to be discreet when he’d check out a woman. I’m talking craned neck, walking backward. Total cheese. Subcategory: F-boy as in “send me a pic babe.” No Thanks!

I do kinda feel bad for them. There will always be someone prettier, funnier, sweeter, hotter, whatever-er. What they don’t understand is that there’s always someone “better” than them too - hotter, more successful, fitter, etc. What matters is that someone chooses you for you and for all of your quirks.

The Rescuer: These guys want someone to take care of, or rescue. They barely know you and they want to spoil you, take you on trips, fly you away and just overwhelm you with stuff. For me, this means strings and a cage. No thanks, I’m not a puppet. I’d rather be single and independent. This does not include someone who is just trying to do something nice for you or be there for you after you’ve gotten to know each other. That’s normal. Pampering is one thing, trying to rescue you or buy your love? No Thanks!

The Narcissist or Control Freak: My worst date was with a guy who spent the entire brunch talking about himself. If that wasn’t bad enough, he proceeded to order for both of us without consulting me and then told me how the food should be eaten with the different sauces. There aren’t enough mimosas in the world to make that tolerable. RUN!

Stage 5 Clinger: Please get off me because I can’t deal with this. I need space. You make me want to move to Mars.

The Guy Next Door: Luckily, most guys seem to fall into this category. They’re just normal, run-of-the-mill nice guys. 

You may see yourself a bit in each of those categories, but these guys take things to a whole different level. Here’s the big self-awareness thing I learned: I’ve been guilty of being in most of these categories while going through my divorce (yep, another reason not to date before your divorce is final or for the first year after). 

We all have baggage. It’s about which imperfections you can live with. Those who are self-aware, warm, genuine and empathetic are the ones who are easiest for me to be around. A guy who is a kid at heart while also being responsible and having his sh*t together would be awesome. 

Dating different guys helped me create a list of characteristics for what I want, which is a helpful exercise. I’m not married to that list, though. A guy can check all of the boxes, but it comes down to that connection. It’s either there or it isn’t. I also learned my process for dating.

Honestly, when I was going through my divorce, besides finances, getting back into the dating scene was one of the most terrifying thoughts I had about being single again. But, it’s been enjoyable. Even the skirt chasers are entertaining. I’ve ended up staying friends with a few of my dates and we have enlightening conversations about the different sexes, dating, parenting and just life.

Finding someone who captures my imagination and lights me on fire is rare. Like “shooting star” rare. I didn’t find that shooting star until after my divorce. It’s like eating McDonald's all of your life and then tasting something from Odd Duck or Trulucks. You just can’t go back to McDonald's. Even if you’re starving, break down and go through the drive-through anyway, it’s never satisfying so you’re just back to square one and craving some crab cakes.

Unfortunately, that shooting star didn’t work out, so I’ll just make a lot of friends in the meantime and hope another comes along. After all, there are a lot of stars and one of them will eventually shoot through the sky.

Because another thing I’ve learned is that there’s a TON of single people and guys are willing to drive and fly for miles just to go on a date with you.

Here’s to finding that shooting star!

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