He still has stuff from his ex around - red flag or deal-breaker?

[TheEvilJester]

TheEvilJester , always a real pleasure to hear from you. Thank you for your tact and empathy in answering my doubts.

Oh, why thank you. I do try. Honestly, I always try to help as best I can with those who come along, and I always try to empathize with the person asking advice... but sometimes there are people that come along that remind me a lot of my own experiences. You happen to be one of those cases where I can relate so much to how you feel/how you think. I've wrestled with a lot of my own self-doubt over the years. I've kind of become skilled at it. LOL!

You know, as I read your entry I remembered something he said on one of our first dates, the first time he mentioned his ex. It is unfortunate that I forgot, because it might be a big deal.

We were talking about Marilyn Monroe, and how apparently she could switch her persona on and off. So then he asked me, if there were a scale in which 1 is masculine and 10 is feminine, where do you see yourself?
I thought of it and answered " I reckon a 9... I like taking care of myself, I like girly things and spending time with girl friends, I'm quite nurturing..." and he said "That's interesting, because I would have put you more as a 5 or a 6". I must have looked a bit taken aback by his words, because he rushed to explain himself, and made the situation worse " No no it's not like that. I mean it makes sense that given the job you have and the life you lead you couldn't really dive into being super feminine or it would come off unprofessional. You see my ex was a lingerie model - someone that appeared on Maxim - and her life consisted of being stopped by guys as she walked down the street. Of course her job allowed her to tap into her feminine side more, so I would say she was more of a 9 or a 10 from that point of view. But she was obsessed with appearances and needed me to let her know if anyone was planning to come over so she could put make up on, and so it didn't work out" not a perfect quote, but close.

In afterthought, I got compared to his ex and lost at sizeable numerical difference. On date 3 or four. Yikes, not a great sign huh.

LOL! You know... maybe... But do you what I honestly think? I think it was more a case of him MEANING it as a compliment, but not thinking at first about how it sounded. Like, it sounded more complimentary in his head. I think we've all done that at some point. Especially us guys. We can be idiots. Then, he either realized you didn't take it as a compliment, or when he heard himself say it he realized it sounded bad... and he panicked. In his panic he just made it worse. ...Again, it isn't like I was there to witness it myself, so I can't know for sure. But from the paraphrased conversation you shared, that does sound to me like him meaning it as a compliment and not realizing until too late that he'd not handled it well. LOL!

Then yesterday we went to a museum together and upon showing me this person he followed on instagram I couldn't happen but notice that the most searched person on there was someone whose name is the same as the ex he's still in contact with. Unfortunately I didn't catch the full Insta Handle (my investigative skills aren't really that great) but I looked for her among the people he follows and she's not among them. So, if I can make an assumption, he looks at her profile all the time, talks to her, but doesn't want her to know he's watching. Which is not great.

You know.... at least as far as the first part of this (him following a bunch of attractive women on Instagram) maybe I can put that in perspective. I'm about the biggest boy scout kinda guy you can ever ask to meet. I am absolutely not the kind of guy who hornily (is that a word) follows a bunch of attractive women thinking I can "hit them up" and maybe actually hook up with one/some of them. Even so, I still follow my fair share of women I happen to find attractive on Instagram. Celebrities, cosplayers, and a lot of the "Suicide Girls." (Side note: If you aren't familiar with the Suicide Girls, it is NOT promoting self harm in any way. It is just "alternative" girls. Gothy, with a lot of tattoos and/or piercings, that kinda thing).

So, I think that is just kind of natural. Now, me personally, if I had a relationship, I'd probably un-follow most of them on Instagram. Not like I'd feel I have to, but it would just feel right to me. But I don't think that is something most guys would necessarily bother or even think to do. I don't think it is terribly concerning that he follows other attractive women on instagram. Heck, I dunno about him, but I often follow a bunch of people on Instagram and then completely forget I followed them until they pop up in my feed. LOL!

As far as him searching his ex... well, that may be more concerning, but even there I am not quite sure. Thing is, you never know. Maybe he USED TO search her a lot but doesn't anymore. She'd probably still show on his most searched accounts even if he no longer did. Either way, though, it might not mean anything. I think that is kind of a natural thing most of us can't help at some point. Looking up an ex just out of curiosity. I wouldn't necessarily worry too much about it unless you start to feel there is evidence that he may not be over her after all.

We did have a talk about where we stood and he did say that he wasn't seeing anyone else but that it was too soon for any labels (this was about 6 weeks in) and at the time I was fine with that, as I wasn't expecting to come out of that conversation as boyfriend and girlfriend but just wanted to know if I should have been seeing other people. Now... I'm not sure I can be "unofficial" for much longer as I'm starting to fall for him hard.

And yeah, I'd like to know what it means when guys follow a bunch of fitness girls, local babes et cetera on Instagram. I likes some of their pictures, he doesn't comment - but as far as I know he could be talking to them over. And they're not the classiest type of ladies... like I won't judge them but we're very different for sure. I understand that he will find a lot of people attractive, I really do. But these ladies aren't all famous ladies, they live in our same city... and this app makes it very easy to get in contact with them. It's not as if they were just random people on a google search... you can definitely communicate with them with ease over Instagram and I just don't feel comfortable.
To be fair, he adds someone new every few weeks or so and he only likes a handful of pictures a week, but it's still tough for me, I'm not going to lie.

On the flip side, and I really feel like I need to give him credit for the things he does right as well in order for you to have the full picture, we see each other 3-4 days of the week. He takes me out to dinner and never lets me pay. I takes me to shows and concerts and even though I always offer to split, he never lets me. He told me I looked like Brooke Shields yesterday, and compliments me a lot. He's slowly opening up to me, he's planning some outings with his friends (I did meet his cousin and respective wife) and sent me dinner invitations and seems very interested in my brother's wedding which is coming up in summer. He also speaks about have children often and he asks for my advice - and actually takes it - very often. He cooks dinner for me, he loves to cuddle and takes pictures with me. He sent my office flowers for Valentine's Day, he takes interest in my problems and seems open to meeting my friends. These all seem to point towards him wanting to be serious, but he could just be a nice guy that wants companionship?

These are my plans:
1.) next time he brings the ex up, I'll ask for more details
2.) I'll date him another 3 weeks or so and see if he makes any plans or refers to me as anything different from a friend in public or tries to bring up the girlfriend conversation
3.) I'll try to see what he has to say about relationships and marriages in general

It sucks because these all tests in some ways, and I don't want to be testing him as he's always very lovely and kind with me, but I don't want to fall for someone that doesn't to get married down the line or who still isn't over his ex.

Anyways... part of this is just me ranting... but the other part is a desperate need for feedback. Keep me sane, please!


PS: the photobooth strip on his fridge is dated 2015 so I guess that's not terrible news. Then again they could have dated for years after that but at least that points to it being remotely in the past.

Okay, so for all the rest of that....

Again, all I really have to go on is what you've shared. It isn't like I can know for sure.... But I will say this. Most of the possibly negative things you mention (things like him following attractive women on Instagram) strike me as being more likely just something all guys do and not necessarily a reason for concern. At least not unless it is excessive, or you ever do find out he's actively trying to date these women. But, to me, that strikes me as just being something people do and not necessarily a cause for concern. Any of the negative things you've shared tend to strike me as POSSIBLY being a red flag, but most likely not being a big deal.

...But then you shared a lot of the positive stuff as well... and all of that kinda makes ME want to date him. LOL! And I'm a straight male. So, maybe it is a case of judging whether or not his words match his actions. If you ask me, at least based on what you've shared, I'd lean towards thinking they very much do match.

Again, though, I'm not close to the situation. I can't know for sure, which is why I do hope you develop the same skills I have for getting a little better at sifting through the BS/lies and the truth. At telling when somebody just SEEMS good on paper and when they actually ARE good. But, for what it is worth, a lot of what I've heard does lean me toward thinking he may be one of the good ones. Best of luck to you as always.