I would not want a date to come down and wait with me so not a red flag for me. I wait for Uber perfectly safely in my friends’ apartment lobbies without company; I don’t see why I wouldn’t be able to in a date’s. But also I dislike overly protective men — there was one who insisted on walking on the street side of the sidewalk like I was a toddler who might run into traffic and that was a deal breaker for ME.

Anonymous wrote:

Anonymous wrote:I don’t think it’s a deal breaker. If you’re 40 and divorced I hope you know to stay outright to him, “I like it when the man in my life is concerned about me getting home safely, could you show you want to hear from me when I get back to make sure I’m safe?”

OP: I would feel totally fine saying this. I guess my concern is if this doesn't come naturally, or he doesn't actually want to do it- what does that mean.

Doesn’t mean anything except you two might not be compatible, which is what dating is supposed to uncover. Red flag is something that is a sign of some universal unfixable issue- this is just a preference on your part.

Anonymous wrote:

Anonymous wrote:As an actual, grown adult who actually manages to get around the city during the day and (gasp) at night, too, I don’t need my date to cosplay Protective daddy and all the messed up power/misogynistic dynamics that come with that. What else do I need protection from? My friends? Voting? Working? Math?

Just not my kink, YMMV.

NP. I wouldn’t have said it like this, but I agree with the poster. I prefer a man consider me a grown woman who can take care of herself rather than some damsel who needs to be escorted to my Uber.

I think it’s a sign that he is not as into you after the date.

Anonymous wrote:I don’t think it’s a deal breaker. If you’re 40 and divorced I hope you know to stay outright to him, “I like it when the man in my life is concerned about me getting home safely, could you show you want to hear from me when I get back to make sure I’m safe?”

OP: I would feel totally fine saying this. I guess my concern is if this doesn't come naturally, or he doesn't actually want to do it- what does that mean.

Anonymous wrote:Red flag is that he’s in his 40s and still in an apartment.

That’s what often happens when you get divorced.

Anonymous wrote:What was he wearing? If he was dressed he should have gone downstairs with you to wait.

OP: he was fully dressed, except for his shoes (was wearing socks).

I don’t think it’s a deal breaker. If you’re 40 and divorced I hope you know to stay outright to him, “I like it when the man in my life is concerned about me getting home safely, could you show you want to hear from me when I get back to make sure I’m safe?”

What was he wearing? If he was dressed he should have gone downstairs with you to wait.

Anonymous wrote:Red flag is that he’s in his 40s and still in an apartment.

Ha! My NYC apartment is gorgeous and worth way more than your shit shack.

He probably thinks you’re a capable, independent woman, who has gotten along without him until now, and can continue to take care of yourself.

Anonymous wrote:Red flag is that he’s in his 40s and still in an apartment.

If he's recently divorced and has payments to make to his kids and former spouse, that's not such a big red flag.

But, yes, OP, I would consider not checking on you to make sure you got home safely a red flag. It's not considerate to not walk you to your Uber - or better yet, offer to drive you home himself - at 12:30am. I am a woman and would do this for a female friend. Not a gender thing. It's a safety thing. How does a man get to age 40 and not know that women are more vulnerable in such situations?

That sounds super old school...

Anonymous wrote:As an actual, grown adult who actually manages to get around the city during the day and (gasp) at night, too, I don’t need my date to cosplay Protective daddy and all the messed up power/misogynistic dynamics that come with that. What else do I need protection from? My friends? Voting? Working? Math?

Just not my kink, YMMV.

Anonymous wrote:Red flag is that he’s in his 40s and still in an apartment.

Strongly disagree. Maybe he works downtown and wants to live within walking distance.