Dear Wendy: “Is 25 Too Old For A Delicious High School Relationship?”

My new boyfriend and I have been “together” for about a month now, but I’m not sure if we have any business dating each other. I’m a single mother and my daughter and I live with my mom. I hate it but I can’t do much else right now unless I decide to put myself in some sort of women’s shelter. I just don’t have the funds and I don’t want to put my little girl in school for the sake of respecting my spiritual beliefs. My boy lives temporarily with his parents, as well. He’s 27 and I’m 25. Neither of us has plans to get a real job any time soon. He’s a photographer and I’m a writer and we’re both artistically productive to a financial fault — it’s hard to market art. Anyway, we have so many shared interests but the financial situation is the one thing that makes this whole relationship feel deliciously high school. I have this aversion to men who would basically be taking care of me. I don’t want to be under anyone’s thumb. And, I know it’s jumping the gun some, but I could see myself living with only just enough to eat, write and be warm with this great guy for the rest of my life. Living simply never seemed more attractive. What do you think? — Two of a Kind

What do I think? I think you should grow up, get a job, and start taking responsibility for your daughter and your life. Woman, you are a mother. Start acting like one! Living with “just enough to eat, write and be warm” is not ambitious enough for someone who is caring for a child. Forget this 27-year-old boho bum with a camera and make the comfort, safety and welfare of your daughter your main focus. And put her in school! Enough with this “spiritual reasons” BS. A child needs an education, and I have a hard time accepting that even if you’re home schooling her — which you make no mention of in your letter — that that’s more important than earning a living to support her, or frankly, that you even possess the skills, motivation and knowledge to teach her lessons that are of any value to her. At least at school, she might have a chance at seeing some role models who can help guide her to a productive life path. Oh, and there’s nothing “delicious” about a relationship between two 20-somethings that feels like it could be between two high-schoolers. A better word might be: pathetic.

I split with the father of my young son nine months ago. We weren’t married, and it was a very messy and traumatic breakup (for me, anyway). Since then, I have had nothing by way of men except a consistent (and good) FWB/ booty call situation, and two isolated hookups. I found myself in a better place emotionally a few months ago, cut off the FWB and decided to try having an actual “boyfriend.”

About a month ago, I started talking to this guy via Facebook. We had several close mutual friends, and he looked kinda good, so I saw nothing wrong with it. At first. I waited about three weeks to have sex with him, thinking that not sleeping with him right away would garner some respect and perhaps help me avoid the “jumping-in headfirst” mistakes I have made in my past. But last weekend, I finally gave it up, and I don’t know what it was about “The Deed” that made me see all the red flags I should have noticed in the weeks leading up to it, but I feel like I’ve been hit by a ton of Mr. Desperate bricks, and I could use some unbiased advice. Here are just a few examples of the triggers making my brain say “RUN!”:

1. While, um, doin it, he said to me, “Do you like me?” and I said, “Um, yes” (I’m having sex with you, right?!) and he replied, “You JUST like me?” and I said, “I like you a lot?” in the form of a question. I now realize that he was looking for the dreaded L-Bomb! Yikes!

2. For weeks — almost since we first met — he INSISTED on putting snow tires on my car. Granted, he is a mechanic/ auto body guy, and I get that it may irk him to see such bald tires on a car, but I’m a grown-ass woman with a child and I will take care of my own damn tires! Well, he harassed me about it so much and became such a JERK about it that, after saying no at least 20 times, I finally gave in.

3. He insists on paying for EVERYTHING. No exceptions. And he keeps offering gifts and luxury items despite the fact that I have already (nicely) declined and asked him not to “be so generous.” This sounds great, but I assure you, it is not under these circumstances. As a recently single mother who raises her son, works full-time and is starting school, I greatly value my independence, and I get the feeling that this guy is looking to “save” a Damsel in Distress.

4. He told me that his mother already dislikes the idea of me because I am a single mother. Gee, buddy … that really makes me want to hang with the fam!

5. He revealed to me the first time we hung out (FIRST TIME EVER) that he had been molested by a man when he was a child. Now, I have the utmost empathy for any sort of sexual abuse victim and have been affected by it personally as well. But to literally blurt something like that, totally out of context, the first time you hang out with a new girl?! Who DOES that?

6. He talks about his ex a LOT. A LOT. Now, I have MANY unresolved emotional issues with my Baby Daddy, but you don’t see me gettin’ into all that mess with my new boyfriend … how inappropriate!

I could keep going, but I feel like he is just the utmost degree of creepy. But, at the same time, I also believe he is a TRULY nice guy, who is perhaps looking to settle down with someone NOW. I feel terrible, but I think I want to break it off with him. Problem is, it’s Christmas. And he just put these tires on my car. I don’t want to be the bitch who made off with $200 tires and ditched him at Christmas!

Do you think I should stop being so nitpicky and see how things pan out through the holidays, or MOA now? — Sticky Sitch

You’re not being nitpicky; you’re being completely reasonable. This guy says and does things that make you seriously uncomfortable, so why would you keep seeing him? For as “nice” as he may genuinely be, he doesn’t need your pity company or holiday “charity sex.” Look, you’ve known the guy for a month and it’s still early December; we’re not talking about dumping a long-term partner the night before Christmas here. And you’re under no obligation to stay with him simply because he bought you new tires. You didn’t ask him to buy you new tires. In fact, you turned him down 20 times before you finally caved. If anything, he sort of bullied you into it, no? At any rate, this is definitely a MOA situation, SS, and the sooner the better!