Anonymous
02/09/2026 13:11
Subject: Re:WWYD?
Anonymous wrote:Yikes! 😬
I wouldn’t jump into this - - reason being is that if you two DO end up dating - - and things go South, your job would/could be awkward or even in jeopardy in the long run……
This. Don’t sh*t where you eat.
Anonymous
02/09/2026 11:35
Subject: WWYD?
The Duke part is a red flag for me.
Anonymous
02/09/2026 09:59
Subject: WWYD?
Anonymous wrote:Not a good job move. Leave him alone as one who got away.
This. Sounds gay anyway.
Anonymous
02/09/2026 09:36
Subject: WWYD?
Anonymous wrote:Anonymous wrote:I’m a 25-year-old woman and was invited to a party at my boss’s boss’s house along with my boss. She is an SVP and was celebrating her 25th wedding anniversary. At the party, I saw her 24-year-old son for the first time. He is tall, very handsome, and recently graduated with a master’s degree from Duke University. He played the guitar and sang a few romantic songs for his parents’ anniversary.
A few people at the party mentioned that he is still single, but I was too nervous to approach him and introduce myself, which I’ve regretted ever since. I even considered asking the SVP for his phone number, but my nerves got the best of me and I couldn’t do it.
How do I go about getting his contact information and letting him know that I’m very interested in dating him? Guys like him aren’t going to be single for very long. For what it’s worth, I didn’t know anyone at the party besides my boss.
Hopefully, SVP and her son are reading this post and will connect with you.
Also, why would the SVP take you to a private party? She wants you to make a move.
What?? The 24 YO son can make the first move if he's interested. He can ask mommy for her contact information. Otherwise, OP should move on.
Anonymous
02/09/2026 09:34
Subject: WWYD?
Anonymous wrote:I’m a 25-year-old woman and was invited to a party at my boss’s boss’s house along with my boss. She is an SVP and was celebrating her 25th wedding anniversary. At the party, I saw her 24-year-old son for the first time. He is tall, very handsome, and recently graduated with a master’s degree from Duke University. He played the guitar and sang a few romantic songs for his parents’ anniversary.
A few people at the party mentioned that he is still single, but I was too nervous to approach him and introduce myself, which I’ve regretted ever since. I even considered asking the SVP for his phone number, but my nerves got the best of me and I couldn’t do it.
How do I go about getting his contact information and letting him know that I’m very interested in dating him? Guys like him aren’t going to be single for very long. For what it’s worth, I didn’t know anyone at the party besides my boss.
Hopefully, SVP and her son are reading this post and will connect with you.
Also, why would the SVP take you to a private party? She wants you to make a move.
Anonymous
02/09/2026 09:31
Subject: WWYD?
Not a good job move. Leave him alone as one who got away.
Anonymous
02/09/2026 07:28
Subject: WWYD?
Anonymous wrote:I would try to find him through LinkedIn or social media and DM him.
+1. Isn’t that how the kids connect today anyway?
Anonymous
02/09/2026 05:26
Subject: Re:WWYD?
Yikes! 😬
I wouldn’t jump into this - - reason being is that if you two DO end up dating - - and things go South, your job would/could be awkward or even in jeopardy in the long run……
I wouldn’t jump into this - - reason being is that if you two DO end up dating - - and things go South, your job would/could be awkward or even in jeopardy in the long run……
Anonymous
02/08/2026 19:58
Subject: Re:WWYD?
Are you sure he’s single now OP?
Anonymous
02/08/2026 19:54
Subject: WWYD?
I also was going to suggest linkedin. Go with that.
Anonymous
02/08/2026 19:49
Subject: WWYD?
I would try to find him through LinkedIn or social media and DM him.
Anonymous
02/08/2026 18:25
Subject: WWYD?
Shoot your shot!
Anonymous
02/08/2026 18:14
Subject: WWYD?
I hope this works out! If I had a grown child, I would think it was really cool if they made a connection through me.
Anonymous
02/08/2026 18:10
Subject: WWYD?
Link up with him on LinkedIn and tell him his guitar-playing was adorable.
In my opinion that's the main reason why guys learn to play the guitar.
LinkedIn is less tacky than other sites. He will also then determine where you are with respect to his mom's job. (He might not be cool with dating her direct report.)
If no LinkedIn, try Instagram.
In my opinion that's the main reason why guys learn to play the guitar.
LinkedIn is less tacky than other sites. He will also then determine where you are with respect to his mom's job. (He might not be cool with dating her direct report.)
If no LinkedIn, try Instagram.
Anonymous
02/08/2026 18:03
Subject: WWYD?
I’m a 25-year-old woman and was invited to a party at my boss’s boss’s house along with my boss. She is an SVP and was celebrating her 25th wedding anniversary. At the party, I saw her 24-year-old son for the first time. He is tall, very handsome, and recently graduated with a master’s degree from Duke University. He played the guitar and sang a few romantic songs for his parents’ anniversary.
A few people at the party mentioned that he is still single, but I was too nervous to approach him and introduce myself, which I’ve regretted ever since. I even considered asking the SVP for his phone number, but my nerves got the best of me and I couldn’t do it.
How do I go about getting his contact information and letting him know that I’m very interested in dating him? Guys like him aren’t going to be single for very long. For what it’s worth, I didn’t know anyone at the party besides my boss.
A few people at the party mentioned that he is still single, but I was too nervous to approach him and introduce myself, which I’ve regretted ever since. I even considered asking the SVP for his phone number, but my nerves got the best of me and I couldn’t do it.
How do I go about getting his contact information and letting him know that I’m very interested in dating him? Guys like him aren’t going to be single for very long. For what it’s worth, I didn’t know anyone at the party besides my boss.