I need advice! my property manger at my complex flirted with me at the bar?

[Anonymous]

So my (lesbian) friend and I went to a gay bar last night (I’m bi). We ran into a guy there who I didn’t know, but later found out was our new property manager at the condos where we live so we all talked and drank together. The whole night my property manager was clearly flirting with me. Gazing, touching my arm/shoulder when he would talk or laugh. My subtle comments, I could tell he was into me with how touchy feely he was with me and the way he was making innuendos all night. He made a joke about needing my number and I replied “you have my information already!” Then he goes “I will need to LEGALLY obtain your number”. We just laughed and then the bartender interrupted. Later, He and my friend started talking about camping so they exchanged numbers and he said he would let her know the best camping sites. Now my friend is an obvious lesbian (she dresses like a Tom boy and has her hair cut like a guys hair cut). When we ended the night he gave me a hug but I was surprised that he didn’t officially ask me for my number. My lesbian friend even made a comment “I think he’s SO into you” but it was hard for me to believe because he never asked me for my number. Guys…. based on his behaviors do you guys think he is genuinely into me or was it just a fun night?

Updates

4 mo

Any opinions?

Updates

4 mo

Any more opinions?

[Oliverlogan263]

This is a tricky situation! On the one hand, the property manager was clearly hitting on you hardcore all night flirty with with the touching, jokes, eye contact, etc. Sounds like he's into you.

But the fact that he didn't actually ask for your number when he had the chance is super weird. Like bro, you were right there! Why didn't you seal the deal?

Maybe he was just having a couple drinks and having fun in the moment, but is worried about any potential issues since he works with you? Like what if things don't work out, could make the living situation awkward

I'd say keep your eyes open for more signals from him. If he starts finding excuses to come talk to you or work on your place extra or whatever, then there's definite interest.

Otherwise you may have to make the first move! Casually mention to him you'd be down to hang outside work someday. But be careful, work romances can easily go south.

Tread lightly for now! Let me know if you need any tips sliding into those DMs if things heat up 🔥

[Asker]

This is very helpful. Thank you so much:) I think he didn’t ask me because my friend was there for most of the time so it would’ve been awkward.

[Oliverlogan263]

Yeah, that makes total sense that he didn't ask for your number specifically with your friend right there. That def would've been awkward!

Him exchanging numbers with her instead was actually a pretty smooth way to still connect indirectly through your friend. Shows he's clever too.

I'd say try chatting with your friend a bit more about him, see if she picked up on any other vibes while they were talking one on one. Maybe she noticed more signs he was feeling you.

Then next time the three of you hang at the bar, watch how he acts around just you without your friend as a buffer. Like I said, try nudging the flirting back a bit and see if he makes a move for your number or something more direct.

If he jumps at the chance, that'll tell you for sure he's really into it. Might feel less risky for him too if he sees you putting out signs you're open to something more.

Just take it slow and see where the vibes go from there, sis! I'll keep my fingers crossed he's really feeling you. Keep me posted on how it goes! 🤙

[Asker]

I’d really hope that was why he was so willing to exchange numbers with her. Like why flirt with me and touch me all night just to never ask me. If that was his motive then it totally makes sense. I forgot to add that the first time he wanted to try the drink I was having so instead of drinking from the cup or using another straw he drank from mines. Then it happened twice that night he drank after me. I wouldn’t finish all of my drink so he took my cup form my hand and drank it. Before we left he had a beer and he passed me the bottle so I just drank what was in there. Not sure if drinking after each other means anything but I just remember that happened throughout the night as well as the other signs. My friend says that because of how touchy feely he was with me she thinks that he likes me, also from how interested he was in talking to me and being playful. But I feel hopeless now because we never exchanged numbers and due to the holiday the managers office is closed….. (he has my number technically but legally can’t use it). I feel so hopeless now, I actually like him!

[Oliverlogan263]

Woah, sharing drinks like that is definitely some pretty big flirting/ intimacy gestures. Almost sounds like he was trying to subtly "indirect kiss" you through drinking from the same cups and bottle. I'd say there's no doubt this guy was super into you based on all the other signs plus sharing drinks like that. That's some major flirtatious body language right there. The fact that he technically has your number through being your landlord also makes it tricky for him to actually pursue you without risking his job. I get why you'd feel kind of hopeless since you can't really make the next move either without that same issue. Ugh that suck man! But don't lose hope just yet. When his office reopens, maybe find an excuse to stop by in person and casually bring up the fun night you had at the bar. See how he reacts just chatting one on one. If he seems just as interested still, you could let him know kinda flirty-like that you'd be open to hanging out properly off the clock sometime. That way the ball's in his court to ask you properly on a more "just friends" type basis. It might help him feel less risky about it than acting on something right away with your number. Stay positive - I still think there's a good chance he's into you too!

[Asker]

Thank you so much for all of your feedback and opinion. You really helped me out more than you know! I will see if the office is open tomorrow because I actually do need a parking permit! So I will eventually need to go there for a genuine concern! I just feel nervous having to interact with him after that night. I’m not sure if it was drunk flirting or genuine flirting!

[Oliverlogan263]

You’re welcome and Ah, I feel you - it's always awkward dealing with someone after a night of potential flirting! But honestly it sounds like this guy was into you for real, not just drunk talk.

When you go to the office, play it cool. Be friendly but not overly flirty since it's a work thing. Just casually bring up how fun that night was again to gauge his reaction. I'm sure he'll be nervous interacting with you too at first!

If he still seems shy and fluster-y, maybe slip him your number again "in case any issues come up." That takes the pressure off in the moment but gets your info to him. And who knows, once that first contact is over you could end up chatting way longer than needed about that parking permit 😉

But don't stress too much - worst case, you get your permit taken care of. Best case, maybe you land yourself a hot new man! You've got nothing to lose. Just be yourself and see how it plays out. Keep me updated! You got this.

[Asker]

I’ll keep you updated:) thanks again for your help you are seriously an amazing person! There’s a slight chance the office will be closed tomorrow im unsure of the hours during the holiday! I’ll send updates!

[Oliverlogan263]

No problem, anytime! I'm just glad I could provide a different perspective to help you out. And yeah, definitely keep me posted on what happens - I'm invested in your story now haha. Fingers crossed the office is open so you can chat with him. But if not, don't stress. Things have a way of working out one way or another. Just be yourself and stay cool whenever you guys do connect again. You seem like a cool girl, so I'm sure it'll go well. Wishing you the best of luck! Remember - stay positive, trust your instincts, and holler at your boy if you need any other advice. Talk soon!

[Asker]

Turns out the office is also closed today so I will try again another day. This is actually killing me 🙈

[Asker]

Do you think it would be weird to add him on Facebook?

[Asker]

Scratch that - I’m not gonna add him on fb! I ended up emailing the office and surprisingly they replied. I asked “Aloha! I need to get a parking permit for my car that’s arriving next week! How should I go about getting a permit?” (I left my name at the end of the email as well as my unit number). They replied “Is that a permanent car? Pass by the office during work hours. 8-4” so I guess I will update again when I stop by. 🙊

[Asker]

I think it was him that replied? I’m not quite sure!

[Asker]

I went by the office to get an updated parking pass, and he 10000% drew out the process. A 10 min process turned into a 40 min process. The last time I got a pass and it took 10 min or less….. I could definitely tell he was drawing it out he asked me to have a seat and everything but he still didn’t ask me about my number or the other night. I could tell in his face he was a bit bashful but the conversation still didn’t turn towards exchanging numbers, nor did I ask. It was pretty much business…. he asked me how I was and some small talk but he didn’t ask me for my number or anything. He did ask me to come back to return some paperwork to him and that was about it. Starting to think it was just a drunk flirty thing and that was it. :(

[Asker]

Also, he made a comment that he saw me walking through the complex earlier!

[Oliverlogan263]

That email reply is definitely a good sign that it was him! Even if he played it cool and official.

And man, 40 minutes for a parking permit? He was totally drawing it out to spend more time with you. No way that process takes that long usually. Dude was totally stalling!

I know it's frustrating he still didn't ask for your number though. Maybe he's just nervous or worried about mixing business with personal since he's your property manager.

But I wouldn't give up hope just yet. The fact he drew out your meeting and noticed you walking around definitely shows he's interested!

My advice would be next time you see him, casually bring up going for that drink you mentioned at the bar. Something like "hey, we should grab that drink sometime when you're off work."

Put the ball in his court and give him an opening. I'm sure if he's still into you, he'll find a way to make plans happen outside of work.

You got this luv! Don't overthink it. I honestly think he's shy, not losing interest. Keep me posted on what goes down! Fingers crossed for you.

[Asker]

Awww you give such helpful advice. I should have pitched that line, I had the opportunity! But I, myself was way too shy and bashful…I’m almost sure he could tell. I remember how bashful he also looked the entire time haha. So my friend and I plan on going back to that same bar on Friday. I told her to invite him and she said “oh yeah I should…free drinks” (haha)….. so hopefully if everything goes as planned I will have the opportunity to exchange numbers with him this time…. i realized that ya, he was at work so he can’t just blatantly flirt and ask for my number. There’s cameras everywhere in that complex and in the office. Honestly, he’s so sweet so I can see him being too shy to be that forward while sober. Anyways. Wish me luck on Friday. 😭😭😭

[Oliverlogan263]

Daaamn, Friday night at the bar is gonna be your chance! Don't even worry about being shy before, we've all been there. Focus on having a fun time now.

But yeah, good thinking getting your friend to invite him too. And free drinks? Jackpot haha. With a chilled out atmosphere and no work stuff in the way, I bet he'll loosen up for sure.

Just be your cool, fun self like at the bar before. Let him see how much you liked hanging with him last time. And when the moment feels right, you absolutely gotta slip him your number this time! No excuses.

You got this. I can tell how into each other you guys are. And with a little liquid courage in ya, I know you'll smash it. Let all your shy-ness just melt away and go get your guy!

You deserve to be happy. I'm rooting so hard for you. Just remember to breathe and be yourself. You're a catch, so go get him tiger! Text me all the deets after, yeah? You got this!

[Asker]

I will most definitely keep you updated:) you have given so much helpful advice! Mahalo🙏🙏🙏

[Oliverlogan263]

I hope he shows up, I really do! And hey no problem at all, I'm always down to help a girl out. We gotta look out for each other, you know?

Just focus on staying positive. Either way it goes down, as long as you put yourself out there and have a rad time with your friends, that's all that really matters. The rest will work itself out.

But I seriously have a good feeling about your dude showing up. Then it's on like Donkey Kong! You're gonna kill it, I know it. So don't stress too much. Just let loose and be your awesome self. You deserve to be happy!

Friday night is gonna be lit. Can't wait to hear all the deets afterwards my guy. You got this in the bag, I just know it. So go get em, tiger! And mahalos for sharing all this with me too - means a lot. We in this together!

[Asker]

I’m gonna PM you from my acct!

[Asker]

Oh wait never mind it won’t let me but here’s what happened: Update:
My friend and I went to that same bar tonight but - we did not invite him we just went alone. While we were at the bar we ran into him there! A few minutes after we sat at the bar we saw him headed towards the restroom and he stopped and greeted us.

After he came from the restroom he stopped and chatted with us and we all had a drink. I could tell he was still shy and nervous to be around me. My friend then left to go to the bathroom (😑) so me and my property manger was left alone. He then made small talk and started telling me about a party that’s happening tomorrow and told me that I should come, so I said, “send me the link!” And that’s when he finally asked me for my number and texted me the link for the event and texted his name.

It seems as though after he got my number he loosened up A LOT. Mind you - we weren’t drinking as much as we was the first night we met.

After we left that bar we went to a karaoke bar that was next door. There wasn’t much seating open except for this large booth. I suggested that he sat next to me, so he came to my side, I got in the booth first then h got in (so that he’s near the opening) and then he leaned back on me in a playful way so I started massaging his shoulders haha.

He then sat up and rested his hand on my leg (we were sitting so close that our legs were definitely touching). Throughout the night at this karaoke place we spent the night basically rubbing each others legs and giving each other the “look” 🤦‍♀️. Meanwhile my friend was sitting across the table from us singing and drinking not really noticing what was happening lol…

[Asker]

We get back home and he texts me “going home?” I said “yeah unless there’s somewhere else I should be?”.

So that’s when he gave me his apartment number (mind you - we live in the same complex).
I go home shower and change and he texted me again to come over so I went to his place…..*sigh*

I get to his place and to make a VERY long story short we ended up having sex!

Afterwards we talked for like 2 hours…. i tried to leave 3 different times but he insisted I stay and talk…not at 5am here I am at home and I hate to say it, but even though the sex was good I regret it! I should have definitely waited but it was a really fun night and he implied that he wants to do it in secret places on the property where there are no cameras 🙈 so I guess you were right all along! Hahaha

[Asker]

We also did not use a condom, he did a very very very last minute pull out 🤦‍♀️🤦‍♀️🤦‍♀️ im so ashamed of myself 😭

[Oliverlogan263]

Woah, that's crazy! Sounds like you had one hell of a night haha. Really stoked to hear it went so well between you and your property manager after all.

But yeah, I get why you're feeling regretful about hooking up so quickly without protection. That was definitely risky behavior on both your parts, especially since he's your landlord too. Always gotta look out for yourself first in situations like that going forward.

I know it's easy to get swept up in the passion of the moment, believe me! But protecting your health should be the number one priority. At least talk to the guy about getting on the same page with expectations and being safer if things continue. An STI could really complicate stuff.

That said, try not to be too hard on yourself right now. You had fun, you learned something - no use crying over spilt milk and all that. Just focus on making smarter choices moving ahead, yeah?

No doubt there could be potential for something cool to develop between you guys. But take it slow and be cautious. And hey, maybe hit me up next time before diving right in haha, I'm always here to talk some sense!

Anyway, sounds like an epic night overall. Stoked for you! Just look out for numero uno from here. You got this - keep me posted on what's up with you two!

[Asker]

I just sent you a follow request. I want to PM you!

[Oliverlogan263]

Okay what’s your name so I can follow you

[Asker]

Check your followers. My name is justmisscurious

[Asker]

A lot has happened

[Oliverlogan263]

Okay I will and will follow you now

[Oliverlogan263]

I followed you

[molonski2]

Certainly genuinely into you , I hardly think he could have made it any more obvious..
Just one question what was he doing in a gay bar?

[Asker]

I guess I’m wondering if it were genuine why did he allow us to go our separate ways without any way to “legally” contact each other? I guess that and when people drink they are more flirty so I didn’t know if that could possible be the case here. Also, I asked him why was he at a gay bar. When my friend stepped away to the restroom, I asked him “so are you gay?”. He replied “no I’m not, I just like to come here because one of the board members partner is co owners do sometimes we get free drinks plus It feels like less judgement here”.

[molonski2]

Strange answer ( gay bar ) , very unusual.

[Asker]

He’s probably bi (hence the less judgement comment).

[molonski2]

Yes , I would think he is.