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The Mailbag, a podcast based on this series, is 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. All topics are on the table.
Episode 10, featuring Ross Bolen, is below.
1. Hey Dillon, feel free to have this on the podcast or the column.
So my new girlfriend’s best friend is coming into town soon. I have yet to meet this friend in person, and my girlfriend wants us all to hangout one night this weekend. Girlfriend wants me to plan stuff around town for us three to do one night. I’m thinking of taking them to a wine/craft cocktail place for happy hour, then dinner at some iconic spot, then probably another bar or two.
Normally, if my girlfriend and I were going out, I’d be paying all night for date nights. I’m wondering if I’m responsible for paying for her friend in this situation where I’m entertaining them both all night. Do I be courteous and pick up the tab at each place plus the Ubers? Or maybe I only pay for myself and my girlfriend? Maybe just myself? We’re all out of school/grad school so everyone can afford a night out. Wondering what you and the gang’s thoughts are.
I think it boils down to this: Is it possible for you to bring it up without sounding like a cheap dickhead? Can you say something like “Hey so do you two want to just split this three ways?” or “Sarah, would you mind throwing a card in?” and feel okay about it? I couldn’t.
I have a feeling I’ll get pushback in the comments for this, but I think the move is to pay for both of them all night. First of all, the Ubers aren’t costing you any extra since you’re paying for that anyway. It’s just one more occupied seat in the car. Food and drinks are costly, I get it, but think of it like this: This is your opportunity to impress both your girlfriend and her friend by picking up their tabs. Seize it and be generous. It’s a good look.
It’s only one night of spending extra and it’s a great first impression to make. Winning over the best friend goes a long, long way. There’s a good chance she insists on paying, anyway.
2. Hey Dillon,
Long time, not my first time, always appreciated your advice, so I’m hoping you’ll be able to help again! Diving right in:
My boyfriend & I are planning to get engaged sometime in the next 6 months. We’re excited–after 2 years of being best friends and (by then) 2 years of dating, we’re so ready to take that next step. Also, both our leases come up in June next year, so it would also be the perfect time to take that other big next step of moving in together. The problem is that my dad would literally never forgive me or my boyfriend if we lived together before marriage, and I don’t say that lightly.
My dad is an incredibly old-fashioned Catholic, and he’s already a little upset about “losing his little girl to another man”, even though he really likes and respects my BF. And while I recognize that I’m an adult, I’ve always wanted to be respectful of how he feels because, well, he’s my dad and I love him. But now, it makes both logistical and financial sense to move in together, and we’ll already be engaged when it happens.
So, we’ve been debating just moving in together and not telling my parents. We live far away from them, my dad and I rarely discuss my living arrangements as is, and everyone else (including my mom and my boyfriend’s parents) would be fine with it. Keeping the secret would be pretty easy. My fear is that if he finds out, it’ll do more damage than being upfront would have. So, what do we do? Stick it out for another year and a half or so of dating/wedding planning and move in after the wedding, or do it when we want and hide it from my dad? I hate the idea of lying to my dad, but I also hate not living with my boyfriend and paying two rents when he’s effectively living with me already.
It would be a pretty big mistake to move in with him while keeping it from your dad, in my opinion. You love this man, so you’ll harbor a lot of guilt throughout the entirety of that living situation. Furthermore, IF he were to find out you did this and lied about it, I imagine that would result in an absolutely brutal fallout with him. He would be angry, hurt, and would lose trust in you, your fiancé, and your even your mom. Don’t do this.
I think your move is to talk to him in person and explain to him you intend on moving in with your fiancé, and here’s why:
“It makes both logistical and financial sense to move in together, and we’ll already be engaged when it happens.”
Your pitch is the above, plus you sell him on the premise that living with your fiancé before the wedding will be beneficial for you two longterm, to ensure you’re as compatible as you need to be to enjoy a long, healthy marriage. You have to win him over.
3. Hey Dillon,
What do you think are the most overrated and underrated types of food or restaurants?
Personally, I think Tapas and Sushi are overrated. I always seem to leave hungry or spend an obscene amount to be full.
Looking forward to your thoughts.
You nailed it with tapas restaurants. I believe the whole idea behind tapas is based on deception. Hey come eat our small plates of food! They’re small and cute and fun and taste good, and since they’re not traditionally sized plates, we won’t charge you as much!
It sounds tight so you go there and learn they’re actually very small and you need to order three of them to equal one full size meal that will fill you up. $36 in food and two 10 dollar cocktails later and you’re dropping 60+ dollars for just you.
I can’t hate on sushi, though. That shit is so good.
4. Sup Mr. Pickle,
The basic deal is this: I am right out of college with a good job, no student loans, and I just found out I’ll be getting some serious cash from the (since passed) grandfather. I have about $4000 of casual debt to my parents for helping me get started, but with my current job I could comfortably pay that off in a year. I’ll be getting in the mid 80 thousands. What should I do?
My current thoughts are: max out my Roth IRA yearly deposit ($5500), pay off my debts ($4000), throw 10k in a savings account, and start investing the rest in a mostly ETF concentrated account.
Any suggestions? I’m 23 so this’ll be a lot more than I’m used to dealing with.
I’ll be honest here. Aside from the obvious — paying off debts, maxing out your IRA and 401 (k) — I’m not too knowledgable about ways to invest in the market. I’ll leave that to finance guys in the comment section. Consider buying real estate, though. That’s a great investment that’s paid off for me.
So I’m 24 and don’t have an insta. I swear I’m not ugly or a serial killer, I just deleted it at some point in college during finals week and never got it back. I feel like I’m missing out and would like to start one but I’m super late in the game. I have so many questions.
Will it be weird starting one at this point in life? What should be my first post? How do I casually ask my friends to follow me? Is it weird if I follow old friends I haven’t talked to in a very long time? Also, I work in the tech industry and it’s pretty common to put insta handles on the contact section of your github account/portfolio site. So should I gear my posts towards my industry? Or maybe do a mix of social/industry posts? Please help!
I don’t know why so many of you feel the need to assure me that you’re not ugly, but I weirdly enjoy it. This has to be the hottest collective readership on the internet.
It’s weird to me that a 24-year-old isn’t on Instagram, but I guess there has to be people like you out there. Yeah, you’re missing out on a lot and it’s time to get in the game. Surely you have a collection of semi-recent to recent pictures in your camera roll that you can slowly start posting to your account. Follow old friends, new friends, work friends, and family. Don’t ask anyone to follow you. When they see that you’ve followed them, that’s when they’ll decide if your worthy of a follow-back.
“Or maybe do a mix of social/industry posts?”
Yes, but don’t overthink this. Just show us pics of you having fun. That’s what we all do..
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I always need emails, too. The more questions I receive, the better this series is going to be, so send me your Mailbag questions to firstname.lastname@example.org and please put “Mailbag” in the subject line.