How To Get Comfortable With Dating Again When It’s Been A While

Following three years of more or less accidental celibacy, I made a vow to go on two dates a week, every week. I’m not a psychologist, but at this point, I am pretty much an expert on first dates. And (not to brag) but I usually get asked out again.

Illustration: Sam Woolley/GMG

During the three years when I wasn’t pursuing romantic or sexual encounters, I got really in my head about what dating would even feel like if I tried it again. After writing about what it’s like to be single for long periods of time, I got a huge response via emails, comments and tweets that indicates it’s a pretty common problem.

If you go a long time without dating, getting back on the horse is hard. You’re pretty sure the horse will fight you, in fact. Maybe you just ended a long term relationship, maybe you’ve been disinclined to leave the house. If you do want to get back out there, here are some of my observations after meeting close to a hundred brand new potential soulmates.

Go On a Lot of Dates!

Full disclosure: I did go on dates during those three years of celibacy. Like, four times, maybe. Because I went out with people so infrequently, I put an enormous amount of pressure on myself and my date. I was incredibly disheartened when they didn’t go well or lead to more. Those bad feelings kept me from trying again, for long periods of time.

By forcing myself to brush it off right away and go on another date, I discovered that bad dates are just statistical probabilities. One bad date doesn’t mean a good one isn’t waiting around the corner, and the more you go on, the less crushing it is when they turn out to be the former.

Dating Apps Are Good

Oh, you hate dating apps? Tough. Yes, you may be crushing on someone who also works silently on their laptop at your coffee shop, but do you know if they’re single? Do you know if they’re interested? If you try asking them out and they say no, are there a hundred other people standing right behind them who are single and potentially interested? Dating apps are an extremely efficient way to check out a lot of people who are looking to date, too.

Download them all, keep your pics updated, your bio brief, and your conversations to the point. You might meet someone organically in real life, but that first date with them will go a lot better if you’ve been practicing.

Ask People Out

Even though I spent plenty of time on the apps, I did eventually get brave enough to ask out people I knew in real life. No co-workers, no exes of best friends, nor anyone else it might cause trouble with. Just people I thought were cute and interesting.

Some said no, which helped me learn how to keep treating people normally after rejection. But some said yes, and we had pretty lovely dates. Though it didn’t lead to a relationship, these dates didn’t cripple our friendships, either. And when you know someone, you can skip a lot of the small talk, which rules.

Set Up Dates Near Your Home

Look, this may sound lazy, but when you’re getting back into the dating world, it’s just better to try and meet up with people somewhere easy to get to. Meet up near your office after work, at a local bar, or somewhere less than three stops away on the train (NO TRANSFERS).

If things don’t go well, you only waste an hour over a drink, rather than three hours over a drink and an epic commute. That feels a lot more manageable. And if it does go well, you can invite them right over to your house…

Bring Cash for at Least One Beverage

Having enough cash on hand to pay for your drinks is helpful. Most bars have card minimums, and you may not want to stay for drink number two. It will also undercut any awkwardness about who pays for what. I personally like to pay for my own drinks on a first date, and it’s nice to skip any negotiating or confusion about that by just throwing down those bills.

Try a Coffee Date

I used to avoid meeting people in the starkness of daylight while drinking a beverage that stimulates my bowels, but now I’m a convert. Lean into the discomfort of making conversation with a stranger and do it hyped up on caffeine. Getting to know someone while sober is good, because you will remember it. Coffee dates also remove some of the sexiness of the situation, which is great if you’re not just looking for a hookup.

And if someone makes you laugh when you’re not drunk, that’s a very promising sign. Plus, coffee is much cheaper than alcohol.

Wear Clothes You Feel Good In

Since you’re saving so much money with these coffee dates, buy a few outfits you feel cute in. I wanted to look hot when I started dating again, obviously. But my sexy wardrobe was outdated. This made getting ready for dates stressful, because nothing fit right or made me feel good about my dope bod.

Once I bought a couple simple tops and dresses I could just throw on, feeling good about how I looked was easier. Whether or not dates thought I looked hot, who knows; but at least they weren’t wondering why I was constantly fidgeting.

Don’t Do Anything You Don’t Want To

Once at the end of a very bad date, I offered my hand to someone to say goodbye. He got upset, saying it was weird to shake hands, so I gave him a hug. On my way home, I felt gross. It was just a hug! Not a big deal! But I didn’t want to hug him and I didn’t have to. Be aware of your comfort level with those sorts of things and know that it’s perfectly all right to reject any kind of advance, requests to meet again, or an insistence you stay for another drink.

There’s usually no reason to be rude to your dates, but definitely don’t be rude to yourself! Respect your time and your person; if someone is making you uncomfortable, leave.

Remember Your Date Is Probably Not the One

Coming to a date thinking you’re about to meet your soulmate always leads to disappointment, and it’s not because people are shittier in reality than in your head. It’s because you’re showing up with lots of ideas about who they are and who they will be to you, rather than really getting to know them. The dream of finding The One is sweet. Making a real connection with another person is sweeter.

Also Remember Your Date Wants to Like You

A lot of people get psyched out thinking their date will notice every enlarged pore on their face, or think their voice is weird, or wonder why they’re wearing mismatching socks. If someone is showing up to meet you, assume they want very much to meet someone they like, and are looking for your good points. Enjoy the advantage of meeting a person who is trying to impress you, too.

Be Yourself

When my mum used to tell me to just be myself, I wanted to murder her. I’m myself every dang day and I’m not winning any awards. But I understand what she meant now. Being myself doesn’t necessarily make people like me, but it makes me like me. I do the stuff that makes me feel strong and cool when I’m not dating, so I can bring that energy with me to a date. Fill your life with stuff you love, so when you meet someone they’re meeting you at your happiest and most fulfilled. It’s very attractive.

You can read more about Aimee’s dating resolution on her blog, 2 Dates A Week.