Want to Ask Out a Guy - Need Advice

Okay here I am yet again Nation asking for advice about a guy.
Anyone that’s been here more than five minutes knows I dont have much luck in this area, but I ain’t no quitter.

You may remember me from such disasters as bald guy 2.0, Marshall, and guy from work.
Well let me present to you today…
The tale of the landlord I like (working title)

Late July I had an appointment to check out a new apartment and upon discussing things in landlords office I realized we had a lot in common. We literally have the same Better Call Saul pop head. We shared much excrement over comic con and other nerd things, but that wasn’t even the best part.
What thrilled me the most was that he talks weird like me. Like this socially awkward rambling, but since we both do it there was never a dull moment or a moment of silence. It was wonderful.
I moved in early August and a shared elevator ride left my face beat red and I realized I really dug this middle aged nerd.
He mentioned he has a daughter , but he is not still with the mom.
I obviously don’t know for sure if he’s single , but he talks in “I”, not we, so the internet said that was a thing.
I went to his office to sign the lease and I told him he reminded me of John Malkovich and he seemed to really be flattered by that.
I was attempting to flirt I guess…
Anyway, more back and forth talk and when I was done I said “um so do you want to be friends ?”
He was like "oh ya for sure "
A few hours later and he texted me casually. We shared random pictures and I talked about stardew valley and showed him a picture of my farm.
He made an effort to keep the conversation going and I was smitten.
The next day I texted him and we talked for a few minutes , but then it ended with me just putting a smiley face. Maybe I should have done more , but I didn’t want to seem annoying.

He hasn’t initiated since and that was Saturday. So Sunday, Monday, Tuesday and nothing.
Can I initiate again? Or is that desperate? If he was into me wouldn’t he do more ?
Can I ask him out ? My birthday is coming up, i could invite ???

Ideas ? Opinions ??

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I think it would be great to ask him out somewhere casual. He clearly is interested. I don’t know what the exact age difference is between you, but that combined with his awkwardness could be holding him back.

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Well his daughter is 19. I’m assuming he’s early 40s and I’m almost 35 .

There is a reasonable possibility that both of you don’t want to come off as desperate.

I say just go for what you want. Maybe it works, maybe not. But if you do nothing, there is a possibility that he is into you, and just didn’t make a move.

At the same time, this guy is your landlord, so that could make it weird. Up to you really!

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Jesus. It’s like y’all have been married for 10 years at this point. Also, TMI.

He’s into you. At the very least, is interested but too much of a pussy to ask you out.

We know

Ok, so this dude has not balls. Like at all. Not sure it’ll work out since he clearly can’t muster up the courage to ask you out.

Ask him out since you clearly will have to be the one to do it. Be prepared for some awkward shit, but knowing you, you already are (I mean that in an affectionate way).

For real, best of luck with this guy - I think he likes you but is a bit reluctant for some reason I can’t discern since all I know about him is he’s a super nerd John Malkovich doppelganger…


Screw Polo. :rofl: I’m king of the slow play. There has never been a woman I wanted to date that I haven’t. It may have taken me a while to get there, but I got there. I’m not completely without testicles. The slow play is a valid approach.

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I feel like “don’t poop where you eat” could not be more relevant to this situation. Not to jinx anything or be pessimistic, but it seems like this could get super-awkward for the long-term if things don’t pan out in the short-term.


Maybe I was just bad at slow playing, I’ve always been much more direct when asking out girls. Never had the time or patience for it -

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I’m glad you’ve rediscovered the ability to be attracted to someone and can envision yourself being happy in a relationship again.

Those are really important.


Yes!!! I agree!!

So while I totally understand the dont shit where you eat concern, its really hard for me to just shrug this off.

Especially since he actually seems really nice… not that I’m a very good judge of character, but I like to think I’ve improved :slight_smile:

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I’d do what I do with my neighbor. Be friendly but keep it clean.


She hits all of the markers at all levels for me. Strongly resembles an ex-gf. Every fibre of my being says “Hulk Smash!”

Buuut there’s my wife. And our kid. And her boyfriend. And the long term/semi-permanent living situations we’re both in. And that’s before we even get to whether or not she’s reciprocal.

It’s a practical effort in exercising boundaries.


Too late:

My advice is to ride out the initial excitement phase or at least wait until the edge has come off it. Then see how you feel. He’ll still be there.

Alternatively, next time you pay the rent, send a text: ‘dear Landlord, I paid the rent today! Could I please get a receipt and a dickpic, K thanks’


I’m wondering, would it be possible to have the relationship you want with him without engaging romantically, at least in the beginning?

I’m by no means an expert, but I imagine you could still spend hours geeking out over comic con or even ranting about life without being in an official relationship


Ask him out for a drink. Have enough to drink that you’re both buzzed but not drunk. Say you have an early morning and ask him to walk you to your car. At your car, turn around, say you had a really good time and go in for the kiss.

Proceed from there.

It’s the boring chicken/rice/broccoli of dating strategy. But guess what? It fucking works.


First off, if a guy thinks you’re “desperate” for asking to hang out, then fuck him. There’s literally nothing you could’ve done to make it happen, and you wouldn’t want to anyway…because like I said, fuck people like that. This is 100% about what you want.

Second off, people aren’t like that! He won’t find it desperate. :slightly_smiling_face: :

So much mental masturbation going on in this thread lol…getting wayyyyyyy ahead of the situation.


Does this really happen? I can’t think of a single guy I know who would be upset with a girl pursuing him. Most of the time (from what I’ve seen) the girls put in zero effort :joy:

Mmmmmmmm yes daddy


Exactly! Hence my second point. The only way I can picture it happening is an insecure guy trying to show off in front of his bros “Look guys, this chick’s desperate!” But then he’ll go respond to her anway in private haha.


No guy has an issue with this. It’s whether this fast tracks you straight onto the f-buddy bus, never to be let off is the question.


Nah, I don’t think the first steps matter. It’s the ongoing dynamics in the relationship that determine this. My wife asked me out first. Then she’d put the onus on me to advance the relationship further by pretending to get mad when I didn’t. I found it so cute I fell for it even though I knew exactly what was going on lol.


A friend of mine did this and kept his relationship secret for several months just because he thought we’d laugh at him.


What? @Spock81 all I can think of is Con Air now lol! What about Cage???

Does he speak like this too hahahah???

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