If you’ve been reading the blog for awhile, you’ll know that I’ve had my fair share of dating disasters, heartbreak, and general life experience in the world of romance. And, like most people, a lot of those disasters could have been avoided if only I had paid more attention to the obvious red flags.

So, today, I’m sharing one of my personal stories (ahem, one of my mistakes) about why red flags should always be taken seriously.

The Guy:

Adam (*not his real name) and I went to school together and reconnected through social media. At the time, I’d just gotten out of a relationship and was in a state of pretty serious heartache (i.e. I was a hot mess). He, on the other hand, was single and feeling fine, but still living with his ex-girlfriend.

That was the first red flag.

I didn’t question it too much, though (big mistake), because his reasons all sounded legit. He said they’d broken up several months earlier, but due to COVID, they were still living together until alternate arrangements could be made. Seeing as there was a global pandemic, I took this at face value.

The other thing about Adam was that his ex-girlfriend had a child – let’s call them “G” to keep things gender neutral. Now, G was his ex-girlfriend’s kid from a previous relationship, so no relation to Adam, but Adam and this ex-girlfriend had been together for over 5 years. During that time, Adam had been raising G as his own. This was another reason why they were still living together. Again, this all made sense to me.

According to Adam, he and Ex-girlfriend were planning to live together until one of them could find another place to live. They were going to continue co-parenting G once one of them moved out. They no longer slept in the same room and hadn’t for over 6 months. Apparently, that’s when they broke up.

Adam explained all this to me while we were still in the “talking” phase of things. He seemed open and upfront, so, again, I took him at his word and agreed to go on a date with him.

The “Relationship”:

Adam and I met up at a bar for our first date. I’d gone to school with him, but we hadn’t seen each other in years, so it was almost the same thing as meeting up with a tinder match. He was handsome, funny, flirtatious.

At the end of the date, we had a mini make-out session before going our separate ways. The only odd thing that happened was that his Ex called him a few times. He ignored it, but when I pressed him about it, he said that she was probably calling to discuss arrangements for some activity that G was doing that weekend.

We said ‘goodbye’ and made plans to meet up again.

Our next date happened a few days later. This time, instead of going out on a date, Adam came over. We watched some Netflix, made out some more, and generally had a good time. No shade to those who sleep with guys early on, but I don’t, so our hookup was pretty PG-13.

Now here’s where things get a bit odd.

The next day, Adam tells me he’s feeling anxious about the fact that he “almost got caught” by his ex-girlfriend. (By this, he meant that his ex-girlfriend seemed to suspect that he was out with another girl when he got home).

Of course, that seems like a weird thing to be anxious about, right? They’re not dating anymore so why would she care if he was seeing someone else? For that matter, why should he have to tell her what he’s doing socially?

When I ask him this, he tells me that even though she DOES know that they’re not together, she still has hopes of reconciling, so he doesn’t want to upset her by flaunting the fact that he’s dating. On top of that, apparently Adam is worried that if his ex-girlfriend does “find out”, she’ll be vindictive about it and keep him away from G.

Ok… that doesn’t seem to make much sense. But whatever.

So, on our previous night together, we’d made plans to go out on a date over the weekend (an actual date, doing an actual activity, in public). He tells me that he doesn’t think it’s a good idea – I guess for some reason, the fact that it was in a public setting and during the day made him nervous that one of her friends would see him out with another girl. (Mind you, we don’t exactly live in a “small town” so this is highly suspect).

I’m not happy about this, but there’s nothing I can do about it. I’m still at least semi-interested, so I tell Adam to give me a call when he’s gotten things figured out and he’s actually able to date. Meaning, when he’s gotten his own place and can be seen in public with me. I figure, no harm no foul right?

Fast forward a few weeks – Adam and I haven’t talked since then, but he sends me a text asking if he can come over and hang out. It’s 10:30 at night.


Uh, no.

So, I tell him I can’t. I’m not necessarily put-off just yet, but I don’t love the fact that he’s asking me to do something so last minute.

He could have taken this well, by saying, “Ok, sure, we’ll try another day.”

You know, like a normal person.

But he doesn’t. He starts pushing – he’s apparently going out of town tomorrow and really wants to see me before then.

At this point, I’m pretty annoyed. Like, listen man, no means no.

I tell him calmly that we can just get together some other time – even if that happens to be in a week or so. He accepts this, but not without being pretty damn passive aggressive about it. (I guess you don’t really want to see me that badly. Too bad, I thought we had a good connection. Blah blah blah).

The next night – that’s right the NEXT FUCKING NIGHT – he does the same thing.

I guess he wasn’t going out of town after all – he tells me his trip is postponed until tomorrow. Again, though, when he texts me, it’s after 9 p.m. And again, I tell him it’s too last-minute. This time, I’m not quite as nice about it.

I won’t get into all the nitty gritty details of that conversation, but suffice it to say, I didn’t like the fact that this guy was seriously trying to overstep my boundaries.

Another HUGE red flag.

Now I’m starting to rethink whether or not I even WANT to see this guy again. But I tell him that he can message me once he’s got his shit figured out (remember, he’s still living with his ex-girlfriend).

The Outcome:

A couple months go by and I get another text from him. It reads something along the lines of “I broke up with my girlfriend and I’d really like to see you again. I feel bad about all the misunderstandings that happened before, but I like you and want to make it up to you.”

Um. Excuse me?

You broke up with your girlfriend? Sir, I thought you already broke up with her. You know, since that’s what you told me and all.

I don’t even bother replying.

Life Lesson: Pay Attention To Red Flags

The takeaway here is in the title of the blog post. But, here it is again: Don’t ignore red flags – EVER. If you think something seems weird, ASK about it. Secondary lesson here, don’t date anyone who’s still “living with” an “ex.”

Thanks for reading! Have you ever had a similar experience? Let me know your thoughts in the comments down below!

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About Author

30ish Lifestyle blogger, relationship "expert," and modern-day agony aunt.
Sometimes humorous, always honest.