12 Steps to Asking Someone out on a (Real) Date

There’s no denying that dating in today’s world is tough. Between hooking up and hanging out, going on a date can be emotionally exhausting. Dr. Kerry Cronin is hoping to change that.

Dr. Cronin is the Associate Director of the Lonergan Institute at Boston College and the Faculty Fellow in BC’s Center for Student Formation. Over the past twenty years, she’s spent time teaching in the Boston College Interdisciplinary Perspectives Program, a Philosophy and Theology program in the “great books” tradition. She also works with undergraduate students in retreat programs at Boston College. She’s a regular speaker on college campuses, addressing topics of student culture and formation.

For the past twelve years, Dr. Cronin has required her students to ask someone out. She teaches her students how to ask someone out on a real date, explaining what their time together should look like, and giving her students steps to follow to ensure a successful date.

“It’s almost like the structure of manners,” Dr. Cronin told The Chicago Tribune in an interview earlier this year. “At their best, manners are supposed to let us know how to act and how to work around social awkwardness, but at their worst, manners make people feel excluded and that there’s some secret way that they’re supposed to act that they don’t have access to. Dating is the same kind of thing — at its worst, it can make you feel like there are normative ways you’re supposed to act, and if you’re not doing that, you’re excluded, you’re out. So at its worst, it can be a really rigid system that only rewards people who are in certain circumstances, but at its best, what it can offer us are ways to navigate social vulnerability and social awkwardness.”

You can find out more about Dr. Cronin’s dating challenge in a new documentary called The Dating Project. The film follows five singles on their journey to find love. Are you intrigued by the prospect of a real date? Here are Dr. Cronin’s steps to asking someone out on a good, old-fashioned first date:

1. Ask someone out on a date in person

date in person

Is it tempting to ask someone out via Facebook messenger or Snap Chat? Yes. Should you do it? No. Instead of staying behind a screen, ask someone out on a date in person. You may be nervous, your sweaty palms may give you away, but it will be so much more personal. Some may label this practice as old fashioned, but your date will appreciate the courage and intentionality you put into the ask.

2. Go on a date within three days of asking someone

date within three days of asking

Asking someone out then scheduling your time together three weeks out in advance can cause unnecessary anxiety on both ends. “It invites drama and sets the stage for unsolicited (or worse, solicited) opinions and advice,” Dr. Cronin advises.

3. Keep in mind this is a date – not an engagement

date not an engagement<

A first date isn’t a proposal – it’s just a chance to get to know someone better. You don’t have to know if you’re going to marry each other by the time you finish your cup of coffee. Having the expectation of getting to know each other can help calm your nerves, too.

4. Honesty and openness are key

openness are key

Far too often have friends of mine been on ‘acci-dates’. One person thought the time they spent together was a date, but the other wasn’t quite sure what to call it. Don’t be afraid to be intentional with the time you’re wanting to spend with another person. “While you don’t have to use the word date,” Dr. Cronin says, “Make sure you’re clear that this is a date.”

5. Someone new

Someone new

“This should not be a date with a person whom you’ve dated before,” Dr. Cronin writes. She wants her students to meet someone new and enjoy good conversation as they get to know someone.

6. The date should last between 45-90 minutes

last for 45-90 minutes

Don’t stress out about planning a six hour long afternoon filled with activities. Instead, plan an activity that lands somewhere in the sweet spot of 45 minutes to an hour and half long.

Read more: Dating and Disagreements: How to Handle Surprise Controversy on a First Date

The first time I spent time one-on-one with Joseph (now my husband), we went to the local county fair and then got dinner afterward. We saw each other for less than two hours, but it was the perfect time for good conversation and getting to know each other a little bit better.

7. Make a plan beforehand

plan beforehand

There’s nothing worse than being asked out on a date only to sit around in the car and ask each other what you should do with your time. “Take the initiative to plan the date,” Dr. Cronin recommends “Show that you respect their time.”

8. If you asked for the date, you pay

you pay if you asked

When it comes time to pay the bill, don’t find yourself staring at each other, arguing who should pay. If you asked someone out, you should pay. “Make it clear – the person is worth the money, and you’re worth the investment, too.”

9. Stretch a $10 bill

Stretch a $10 bill

Don’t avoid going out on a first date because your bank account is a little tight. You can have a good time for a little cash. Dr. Cronin recommends just having a $10 bill.  “You’re not a spendthrift, but you’re not royalty either. Unless you are. Then still $10.”

10. No touching

No touching

Keep things uncomplicated by limiting how much physical touch you have on the first date. How far is too far? Dr. Cronin’s answer is that “an ‘A-frame’ hug at the end of the date is enough.”

11. Tell three people you know about the date

Tell three people about the date

Getting nervous before your time together is completely normal, but it’s far less likely to happen if you’re surrounded with support. This doesn’t mean you should tell everyone you interact with about your upcoming date, though. “Only three teammates,” recommends Dr. Cronin.

12. Go solo

Go solo

Sure, you’ve got three friends who know about the date and are holding you accountable. “But for the love of Pete, no wing man, best friend, or group dates,” Dr. Cronin requires her students.

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