It's okay for my BIL to make a pass at a single woman he sees at weekday Mass, right?

[Anonymous]

I hope this is okay to post here. I want to avoid callous comments in the relationship advice forum.

My husband and I are certainly out of touch with modern dating but we think this would be not only totally fine but actually really sweet?

BIL stayed with us this weekend at our family beach house. He is ten years younger than us, handsome and fairly successful. After a long lapse, he shared he's been going to weekday early morning Mass once or twice a week, on days he has to be in the office.

He then said there's a cute woman his age who seems to be there most times he's there. She also appears headed to work. He said they both acknowledge and smile at each other from afar but he thinks that could just be because they seem to be the youngest there.

We insist he has to position himself for an introduction and ask if she's single. Park next to her, hang back at exit after service ends, whatever. He is convinced that is inappropriate and if she's not single or he gets rejected, he'll be too mortified to go to that service again.

[Anonymous]

Tell him to invite her for coffee. Or he can ask the priest.

[Anonymous]

Boy have all men lost all game? No, you don’t go from zero to asking someone for a date in a place where she comes for a purpose other than dating. He would deserve to feel like he could never go to that mass again. He has to actually talk to her, assess if she is interested, then subtly find out if she has a boyfriend. Getting more involved in the church community is also a way - he can ask mutual friends or even the priest.

[Anonymous]

As long as instead of "making a pass" or "hitting on" this woman, he introduces himself, starts small talk, tries to find out whether she's attached, and eventually asks whether they can meet after mass to go for a coffee... yes, it's perfectly fine. And yes, he has to be fine with seeing her again at mass if she says no. He needs to understand that even in 2025, as a man, he is expected by many women in the US to make the first contact.

Just don't be vulgar, OP, and say "make a pass".

[Anonymous]

The language “make a pass” is very old-fashioned, which gives some insight into how you or he are framing it? I usually think of that term as something used in the 70s when someone tries to express physical interest in an inappropriate context. Lol

He can express normal non-lascivious interest and ask her for coffee sometime and if she says I’m sorry I’m in a relationship or I’m sorry I’m married or simply no thank you, then he can still continue to go to that mass. It would be a totally appropriate thing for him to do, but it’s up to him as to whether or not he wants to take the risk of rejection.
If he doesn’t want to take that risk because he would be too mortified to go to that service again, then maybe it’s not the right move for him.

[Anonymous]

Anonymous wrote:As long as instead of "making a pass" or "hitting on" this woman, he introduces himself, starts small talk, tries to find out whether she's attached, and eventually asks whether they can meet after mass to go for a coffee... yes, it's perfectly fine. And yes, he has to be fine with seeing her again at mass if she says no. He needs to understand that even in 2025, as a man, he is expected by many women in the US to make the first contact.

Just don't be vulgar, OP, and say "make a pass".

Sorry, I guess I am out of touch! I truly had no idea make a pass had creepy or negative connotations. Just meant it to mean introduce himself and ask if she'd like to grab a coffee or something, exchange numbers, and go from there.

[Anonymous]

Anonymous wrote:As long as instead of "making a pass" or "hitting on" this woman, he introduces himself, starts small talk, tries to find out whether she's attached, and eventually asks whether they can meet after mass to go for a coffee... yes, it's perfectly fine. And yes, he has to be fine with seeing her again at mass if she says no. He needs to understand that even in 2025, as a man, he is expected by many women in the US to make the first contact.

Just don't be vulgar, OP, and say "make a pass".

He should talk to her for weeks before he asks her out. in this context he should figure out if she’s interested first.

[Anonymous]

Anonymous wrote:Boy have all men lost all game? No, you don’t go from zero to asking someone for a date in a place where she comes for a purpose other than dating. He would deserve to feel like he could never go to that mass again. He has to actually talk to her, assess if she is interested, then subtly find out if she has a boyfriend. Getting more involved in the church community is also a way - he can ask mutual friends or even the priest.

His last few girlfriends were really cute, so I think he has at least some game. I think he just has it in his head it's creepy or even sort of sacrilegious to try to chat up a random woman at church, especially when he just started going to Mass again.

[Anonymous]

I think it's totally okay for him to introduce himself and show interest.

-signed, single woman who occasionally attends weekday Mass

[Anonymous]

Anonymous wrote:

Anonymous wrote:Boy have all men lost all game? No, you don’t go from zero to asking someone for a date in a place where she comes for a purpose other than dating. He would deserve to feel like he could never go to that mass again. He has to actually talk to her, assess if she is interested, then subtly find out if she has a boyfriend. Getting more involved in the church community is also a way - he can ask mutual friends or even the priest.

His last few girlfriends were really cute, so I think he has at least some game. I think he just has it in his head it's creepy or even sort of sacrilegious to try to chat up a random woman at church, especially when he just started going to Mass again.

If she’s repeatedly making eye contact with him, then there’s some likelihood that she’s slightly interested or curious or at least not full out rejecting him. Maybe she’s just being polite and if she’s not interested, she’ll tell him and he’ll act appropriate and all will be fine.

[Anonymous]

Anonymous wrote:

Anonymous wrote:Boy have all men lost all game? No, you don’t go from zero to asking someone for a date in a place where she comes for a purpose other than dating. He would deserve to feel like he could never go to that mass again. He has to actually talk to her, assess if she is interested, then subtly find out if she has a boyfriend. Getting more involved in the church community is also a way - he can ask mutual friends or even the priest.

His last few girlfriends were really cute, so I think he has at least some game. I think he just has it in his head it's creepy or even sort of sacrilegious to try to chat up a random woman at church, especially when he just started going to Mass again.

Well he has good instincts! He just needs to be very subtle about it and maybe even gain some allies to learn about her.

[Anonymous]

Maybe start a conversation about the homily that day and then see where it goes from there? Even if she’s not available, it might lead to a friendship and she might introduce him to other like minded young people. Maybe she knows about groups for young adults at the church that he could join.

[Anonymous]

If she’s single I bet she would be absolutely thrilled. If she’s not single, she’ll at least be flattered if he does it in a nice way.

I think he can just make some basic comments about something like the weather or the flowers blooming in front of the church or whatever. If she chats back, odds are good that she’s interested. He could say something like “I’d love to get a coffee some day when we aren’t both rushing to work.” And if she says I’d love that too, you know she’s interested. If she’s like vaguely “oh maybe sometime….” Or says something generally unenthusiastic, I’d leave if ne. It’s only creepy if he is persistent after being given signs that she’s not into it, or a flat out no. And then be gracious about the no.

[Anonymous]

I would not bet on her being single. If this was weekend mass and she’s solo several weeks in a row, sure, probably single. Solo at early a.m. weekday mass could be anything from single to happily married with kids.

[Anonymous]

Anonymous wrote:

Anonymous wrote:Boy have all men lost all game? No, you don’t go from zero to asking someone for a date in a place where she comes for a purpose other than dating. He would deserve to feel like he could never go to that mass again. He has to actually talk to her, assess if she is interested, then subtly find out if she has a boyfriend. Getting more involved in the church community is also a way - he can ask mutual friends or even the priest.

His last few girlfriends were really cute, so I think he has at least some game. I think he just has it in his head it's creepy or even sort of sacrilegious to try to chat up a random woman at church, especially when he just started going to Mass again.

It's not creepy or sacrilegious to chat up a fellow mass-goer who he sees a couple or few times a week. Like, say "Good morning" the next time. Then a time or two after that he can introduce himself. After that, maybe ask if she's going to the spaghetti dinner next week (or whatever) and mention that he's volunteering. A couple more conversations and he can ask her out. At that point he should have a good idea what her reaction will be.

I mean, where better for him to meet someone that shares his religious beliefs, which seem important to him. I don't usually like to go hard on the "God has a path for you" bit, but maybe in this case it's true?