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The Mailbag, a podcast based on this series, is now live. The questions that make the podcast will be a combination of emails (if you’d like to remain anonymous) and voicemails. The hotline number is above. Please give me plenty to choose from so we have interesting topics of discussion.
Episode 5, featuring that boy Dave Ruff, is below.
1. Hey Dillon,
Love the column and the podcast (I may lowkey be in love with your speaking voice). I have kind of a solemn question for you. My mom passed away last year and we were extremely close. I’m single and in the dating game, but don’t know how, when or even if to bring up that fact when I’m out with someone new. Occasionally on dates, the topic of our parents can come up and when I fill them in, it’s a bit of a mood killer. Is there a right time to tell someone? Should I try to avoid parent talk all together? Or is it not a big deal/too much baggage? It’s not like I get all emotional when I talk about it, but it is an important fact about me since it has shaped some of my life decisions. Any insight from the male perspective is greatly appreciated.
Love you – bye!
First of all, I’m very sorry to hear about your mom. I know that’s tough.
I think the move is to wait for them to bring up family or parent talk first, then, when you share the news of your mother passing, you deliver it matter-of-factly, not solemnly. They will react according to your energy. If you go with a head-down, sad delivery, it’s going to be a mood killer. If you say, “My dad is retired and lives in Chicago, but my mom passed away last year. I get to see my dad every few months,” then the conversation should move forward just fine after he hopefully acknowledges the news of your mom.
Save the deeper mom talk for when you two know each other on a more suitable level. It is not even close to baggage, though. Come on; you know that.
2. Hey Dill Dill,
Comin’ in hot with a cry for help in dealing with a friend.
I have this friend who has, in recent months, become obsessed with her tennis coach from high school. They reconnected this summer after she moved to her beach house for the summer between jobs and started back up with tennis lessons (I know, this is all sounding rather bougie already).
A very important aside: she’s 23 and he’s 33/34.
They started hanging out outside of tennis lessons in the mid-late summer, and would go out to dinner 1-3 times a week. He would pay most of the time, apparently. A few weeks ago, she bought him a helicopter ride-tour thing over the beach town/island as a surprise (about $250). They now seem to be pretty good friends, and she’s absolutely convinced they’re going to end up in a relationship, but he has not made a single move (no kiss, nothing), and has even said that he loves having her as a friend after she told him she liked him. After this occurrence, they have continued to hang out and get dinner, and the other night he slept at her apartment in the city in the SAME BED, and not a single move was made by him.
As her friend, it’s a really weird and annoying situation to hear about all the time, especially considering she thinks that they’re “practically already dating” and is CONVINCED it’s going to happen. I’m even more frustrated with this guy for leading her on like this, while knowing that she’s into him; it feels like he’s using her. Also, he texts like a 7th grade boy (read: “ur 1 of my fav’s in my life rn”, “pretty amaze balls!!”, lots of emojis in place of actual words).
A lot to unpack there, but as someone around this guy’s age, maybe you have some insight as to what’s his deal? Is he using her? Just lonely? Into her? I’ve tried being honest with her about it but can’t seem to get through.
Thanks a mill, Dill.
Mid to late summer is when they started hangin out, so it’s been, what, two or three months? No kiss after a couple months of “dating,” a helicopter ride, and same-bed sleepovers? He’s clearly not into her beyond a basic friendship. It couldn’t be more clear, actually. He also might be gay. Either way it’s the same outcome. I’m not even sure he’s leading her on since he told her he likes her as a friend. Your friend is wasting her emotions and efforts on this guy. Period.
A grown ass man texting like that makes my skin crawl. His squad needs to be made aware of this texting behavior so they can roast him off the face of the planet.
I have an important question that none of my real life friends can come up with a straight answer for, so naturally I’m going to turn to my favorite internet stranger.
I recently joined the world of dating apps. I matched with a guy named Noel and have been on two dates with him and things seem to be going well. When we initially met we went in for the hug and the “how are you?” etc. I didn’t shake his name and say “Hi I’m ____” because he already knew who I was an this is not a job interview.
So now I’m two dates in, and in my head the name Noel is pronounced like “Knoll” if its a guy and “No-Elle” if its a girl. However, I was recently watching the Real Housewives of New York and Countess Luann pronounces her son’s name as “No-Elle”. He hasn’t said his name in two dates and its obviously too late to just ask what his name is.
1. What is the proper pronunciation of the name “Noel?”
2. If #1 can’t be answered, what is the best way to approach this situation moving forward without looking like the self-absorbed idiot that I am that doesn’t know how to pronounce his name?
Keep up the good work!
1. In all my life, I’ve never heard a name pronounced “Knoll” before. From what I understand, anyone named Noel pronounces it “No-Elle.” Like the Christmas song.
2. Just ask him.
Alright so I’m sure you’re gonna tell me what I don’t want to hear BUT I’ll let you do it anyway. Sorry this is so long, I’m a horrid story teller and ramble like no other. But you can prob already tell.
Anyway, I drunkenly slept with this dude one night last semester after he had already slept with one of my close friends for a considerable period of time. She decided to forgive me (after calling me some super rude names) and said I could never do it again.
What did I do? Did it again. I just couldn’t help it, this dude is D1 in bed. A real first round pick. But this dude and I were just friends. He’s a hook-up only typa guy while I’m normally a relationship only typa gal but I liked doing this with him. We slept together twice and then I went home for the summer. We kept in touch for those 3 months I was home, and he got a girlfriend (me and his friends put bets on how long they’d last – I gave them until the end of summer. I won). So clearly he wasn’t with this girl by the time I showed up back in town. He helped me move into my apartment and then we slept together that night out of the blue. I decided to make a play for this man, really try to date him and make him settle down and all because I (might?) really like him. My plan did not work though, as I hit him with the “sooo are u coming over or no” after I saw him at the bar last night and he didn’t read my bootycall message until like brunchtime today and didn’t even reply to it. So freakin rude.
So here’s my question. Do I abandon my hopes of taming this alley-cat of a man, or do I keep going with my valiant efforts to domesticate him? If I keep going, I need some pages from your playbook.
Thanks and sorry this was so long but I gave you fair warning so no complaining.
What is it with girls and wanting a project relationship? You want to train a guy who doesn’t want to be trained. You think if you re-wire the way he thinks and what he wants from girls and relationships, he’ll be all yours for eternity. But that’s just not how shit works. It’s a daunting endeavor that will not work out the way you hope.
Here’s a little secret: He’s not going to be the relationship type until he wants to be, not when you want him to be. It may happen when he meets someone he thinks is worth committing to or it may happen when he’s finished with this current “alley-cat” phase of his life. Either way, it’ll be on his terms and his terms only.
Don’t waste your time..
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