So you’ve matched with a promising guy or gal, and you’ve shared some witty banter on the in-app chat. What’s next? I recommend that my clients schedule a screening phone call. Yes, a phone call.1 This may sound old-school (and tends to particularly weird out millennials), but hear me out. There are a few advantages to doing this before setting up an in-person date: It’s a synchronous communication format with very low overhead. You don’t have the lag of texting, and you also don’t have the scheduling and primping overhead of meeting IRL. The level of investment is somewhere between messaging and getting together, so it’s a nice intermediate step. A corollary is that the downside risk is low — if the chemistry or alignment isn’t there, you can get out in a few minutes. How many dates have you had where it was obvious within the first few words that it wasn’t a good match, but you felt obligated to sit through it for a while anyway? Not so with a phone call! You can assess non-visual cues that can indicate whether or not you have a good connection — e.g. do they have a pleasing vocal tone, are they able to hold a good conversational cadence without talking over you, do they have a compatible sense of humor? It provides enough distance where you feel safe opening up, yet close enough that you get a sense of building rapport and connection. This means that you can figure out if someone’s willing to “show up” to the conversation. Can they have a meaningful dialogue? Are they comfortable getting vulnerable? Before jumping on a call, there is some homework to do first. Part of creating a successful phone screen is coming up with an idea of what the guiding questions for the conversation are. A good phone screen question has two key characteristics: ...

When I got married, it would’ve been helpful to have a blueprint of how other couples structured their finances. The below system is a possible way of doing it, using three pools — one joint and two individual. The joint pool consists of at least three accounts — savings, checking, and investment accounts. The individual pool for each spouse consists of at least a checking account per individual. With these accounts in place, income is allocated to accounts as follows: ...

When my ex-wife and I divorced, sorting out the financial side was the biggest logistical headache that we had. Not wanting to deal with this overhead in the midst of the emotional challenges we were facing meant that we put off formalizing our divorce for a long time. Taking just two simple steps before tying the knot would have made our lives significantly easier. The first step is to know the separation rules for your state as they pertain to finances. Notably, you may not have realized that everybody has a prenuptial agreement (a “prenup”). If you and your partner haven’t crafted your own, you get the state default version. There are two main schemes for dividing assets and liabilities between you and your spouse: community property and equitable distribution. ...

Suppose you want to hire an assistant to alleviate the mundane tasks of your job. Every day that you have the job search open, an assistant comes for an interview. Immediately after the interview you have to choose whether to hire or not hire the interviewee. The hire/no hire decision is irreversible — i.e. if you reject someone, you can’t later decide to hire them. Under these conditions, how do you determine which candidate to hire? The trade-offs are intuitive: if you don’t hire, you incur the overhead of interviewing and don’t reap the benefits of having an assistant; if you hire too early, you may be missing out on a better assistant that’s potentially coming up as a candidate. ...