Awkward Money Situations While Dating

Life is awkward. I am awkward. We're all a little weird and unsure how to handle certain situations. It's okay and it makes it less awkward if we all just acknowledge we're a bunch of social freaks with generally good intentions.

Some of the most awkward situations in life involve money and dating. Individually, both topics are daunting, but combined they are a recipe for cringeworthy levels of uncomfortableness.

So I'd like to take this time to give you my personal advice on what you should do if you encounter common awkward money situations while dating. This is my personal take, it's not written in stone and you're free to disagree. Also please note, if I encountered these problems in real life I'd most likely crawl up under the nearest table, hide in the fetal position, and close my eyes until the awkward moment passed. Don't be like me.

Here we go!

Who should pay for the first date?

Personally, I think if you ask someone out then you should pay for it. I don't think you can expect the other person to pay or go Dutch treat if this whole thing was your idea. This advice is applicable to everyone regardless of gender or sexual orientation, too.

When do you start talking about money in a relationship?

Ummm it depends. Relationships move at different speeds. I know people who dated for nearly a decade before they moved in together and I know people who were engaged after three months of dating (My parents! They've been together 32 years now). Conversations about money should begin if you're considering moving in with each other or the topic of marriage has been broached. Honesty is always best, so don't lie about your student loans or your credit card debt or how much money you make.

What do you do if you and your partner come from very different economic backgrounds?

This happens fairly often. One person in the relationship will come from money while other does not. It can be weird, but it's important to remember why you're dating this person in the first place. You like each other, right? Again, communication is key. It's okay to talk about the different circumstances in which you were raised. Talk about your views on money (in a loving and understanding way). Discuss your differences. You might find you each have differing strengths when it comes to money, so how can you meld those to form a team? Never make your partner feel bad about how they grew up because that only creates resentment and breaks down the foundation of your relationship instead of building it.

What do you do when your partner has a lot of bad spending habits?

This is tough. If this person is someone you want to build a future with, then you really need to sit down and talk about it. Tell them you love them and want a future with them, but you're concerned that their hard earned money won't be used to achieve the goals you'll set as a family. Without being condescending and accusatory, start with leading by example. Show them how you use credit wisely. Ask them if they're saving for their personal goals. Let them know you're concerned, but only because you want what's best for them.

What do you do if you're dating someone who wants to go out all the time and you can't afford it?

Tell them it's not in your spending plan right now and that you're saving for certain goals. Be honest but offer cheap or free alternatives so they know you're not just blowing them off. Tell them you like to occasionally have nights in watching movies or playing games. I think we tend to make this particular awkward situation bigger in our heads. If they don't want to Netflix and chill every now and again, then they aren't that into you anyway.

Got another awkward dating-money question for me? Let me know!

Hey, before I let you go, have you pre-ordered my new financial guide? It's only $2.99 and will help you get your financial sh*t together. It's fun, it's informative, and easy-to-follow. No jargon. No condescending advice. No judging. Just me, you, and a little financial motivation. xoxo

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