Photo: Dumb and Dumber / New Line Cinema

The Most Inappropriate Times Men Asked Women Out

Voting Rules
Vote up the date proposals that deserve a resounding 'no way, dude.'

Approaching someone to ask them out on a date can often be awkward - especially if you use a cheesy pickup line – but there are times when it's flat-out inappropriate. Some people are bold enough to ask women out during funerals, at work, or even in the maternity ward. These are some of the most inappropriate times men came up to women hoping to walk away with a date.

Photo: Dumb and Dumber / New Line Cinema

  • 1
    1,689 VOTES

    A Paramedic Who Saw Her In A Trauma Unit Asked Her Out

    From Reddit user /u/OnATurningCarousel:

    I came with my grandfather to the trauma unit of our local hospital.

    The guy I kinda know from my partying era (but never showed any interest in) was a paramedic there. He messaged me through FB and asked me why I "didn't take off my coat and give them something to look at" and asked me if I wanted to have sex in the ambulance.

    Beyond gross and absolutely inappropriate.

    Edit: how I got out of the situation: I told him I would report him to his supervisor. This crossed all limits.

    1,689 votes
  • 2
    1,375 VOTES

    Baby Daddies At The Maternity Ward Asked The Receptionist Out

    From Reddit user /u/Joonami:

    I work the reception desk on a maternity ward in a hospital. Plenty of baby daddies find my customer service demeanor to be a green light for their affections.

    1,375 votes
  • 3
    1,053 VOTES

    A Car Mechanic Offered Her 'Under The Table' Repairs At The Shop

    From Reddit user /u/kiwitathegreat:

    I once had a mechanic get my number off the RO [Repair Order] and text me offering “under the table” repairs with no effort to disguise the innuendo. I freaked the f*ck out because that RO had all my personal information on it, he knew what I drove, and he knew where I worked. Handled it by completely ignoring the text and watching over my shoulder for months afterwards. Also had my boss mention it to their shop foreman because our businesses would send each other customers and god only knows who else he tried that on.

    1,053 votes
  • 4
    1,185 VOTES

    He Asked Her For Gas Money, Then A Date, At A Gas Station

    From Reddit user /u/Lavender_Pixie:

    I'm not sure if a gas station qualifies as an inappropriate place, per se, but the way this happened seemed very inappropriate at the time.

    A man walked up to me while I was busy holding the pump, which is already kind of an uncomfortable spot to be in (especially at night), and at first he just asked for gas money. OK, no big deal. It happens. I told him I had no cash, and he went back to his (very nice, new-looking) truck. I thought it was a bit weird, but continued pumping my gas and minding my own business.

    Less than 30 seconds later, he walked back up to me, told me I was really beautiful, asked if he could at least get my number, and started begging me to go on a date with him. He said that he would pay me money for a date (even though he JUST asked for gas money). First it was $500, and then it escalated to $1,000 after I said I wasn't interested. He begged one more time, "Just one date, please, just go on one date with me."

    I gave him a final, resounding "NO," finished pumping my gas, and hurriedly climbed back in my car to leave.

    The situation was just very uncomfortable, and I don't particularly like being approached when I'm in a vulnerable situation (pump in hand, on the other side of my car from the driver's side door, etc.).

    Ultimately, I learned that talking loudly, saying "NO" with some force, and looking them in the eyes tends to help in escaping the situation. If I had been more timid and tried to be too "nice," I have a feeling it would've been a lot harder to get rid of him.

    1,185 votes
  • 5
    1,176 VOTES

    Her Uber Passenger Asked Her Out

    From Reddit user /u/kayaking_gnome:

    So I’m a young female Uber driver and I have the same problem but on the other end. I’ll pick up drunk guys and they’ll be so inappropriate with me; it’s really frustrating. I had to start carrying pepper spray at night after one guy had me drive him out to the middle of nowhere and then wouldn’t get out of my car. I’ve also had guys give me low star ratings because I wouldn’t give them my number.

    1,176 votes
  • 6
    959 VOTES

    The Dad Whose Kids She Babysits Asked Her Out

    From a deleted Reddit user:

    I've had several guys try to set up a date while they pick up their squirmy toddler from the daycare I work. Normally I just tell them their kids probably needs their attention.

    I also do a lot of babysitting, most of my customers are just the parents whose kids go to my daycare. All of them have my number too. A couple of dads have tried to get flirty texting.

    For that I'll just start a group chat with both mom and dad. I'll be like "we can continue our conversation here Mr. So&So."

    I've had a couple weird things happen when parents come home from their date nights too but I don't want to make this post to long.

    959 votes