We caught up with professional matchmaker Anne Marshall, the owner of Junia Matchmaking services – junia.ca. Anne helps people improve their dating profiles and helps them find love. We know the dating scene has changed a lot since we were in our college days, and with kids in tow and a career, household, bills, and all of the other fun that comes with adulthood, love and romance can take a backburner. But mama’s got needs, and getting back into the dating scene can be hard, so we asked this matchmaker the things you know you want to know about getting back into the dating scene.

1. How long should you wait after a breakup to get back into dating?

There’s no set formula for determining whether you’re ready – it’s really a matter of feeling like you are. However, a smart person I know once told me (after the breakup of my 8-year relationship) that I could expect to grieve about one month for every year we were together.

I have no idea what her inspiration for saying this was – I’ve actually looked to back it up, and found no source – but it turned out to be very true in my case. Since then I’ve noted similar patterns with shorter relationships (1 month together equals 1 week of feeling bad after being dumped).

In instances where you were the one who instigated the breakup, of course, these timelines might look very different. It’s also important to have an idea of what kind of relationship you’re seeking when you start dating again. Some are looking for more serious commitments than others. I definitely wouldn’t advise going straight after the Next Big Love, in any case. Take some time to enjoy the process of dating, and being single while it lasts.

2. “The dating scene has changed since I was last in it” or “I was with my ex since high school, I’ve never been out in the dating scene” are 2 very common concerns, how do you address these concerns?

Even if you were last in the dating scene three months ago, it has always changed.

I think the worry that you’re doing it wrong is pretty universal. When it comes to online dating, which is probably the most popular way for people who have had children to put themselves out there again, you really have to take a few hours to learn the ins and outs of a particular website that they want to use.

I mean, if your grandfather’s on Facebook and your Aunt Helen has an Instagram, there’s no excuse. These are platforms that anyone can navigate if they really take the time to explore and learn. Go through the entire tutorial and save yourself months of frustration! But many people won’t bother, or fear the technology for whatever reason and just have convinced themselves that they can’t do it. So I run an event a few times a year called the Modern Dating Boot Camp, in which I basically school people in the best practices of navigating online dating in general, and them some of the more popular dating websites. If they attend that session and they still find they can’t or don’t want to do it for themselves, then they hire me. I also have to recommend a great book published last year: Modern Romance, by the comedian Aziz Ansari. It’s hilarious, and absolutely full of good advice for those who might be feeling overwhelmed at the thought of dating again.

3. Is online dating really safe?

I believe that it’s no less safe than “traditional” dating, which means it’s as safe as you can make it. There was a story in Vanity Fair about a female producer from NBC News, who was romantically duped and financially defrauded by a so-called “celebrity surgeon.” He made an utter fool of her and there were many red flags along the way, but even a woman as accomplished as this, with a hard nose for news, failed to follow the basics.

Here’s one: don’t deliberately seek a relationship with anyone who lives more than about an hour away. Why would you? Don’t give anyone big gifts of money, or pay for them to come and visit you with your credit card. If someone says he’s the Pope’s best friend, don’t believe him! Keep your spidey senses intact, and follow the basic rules of common sense: don’t date long distance, and don’t give away your money or your ID, and you’ll be fine.

4. I’ve met someone. How long should I wait to jump in the sack (a momma still has needs!)?

This is tough. It’s a personal choice, and there is no correct (or incorrect) response.

I know of many good, lasting relationships that began as nights of passion; I also know that many people would need to really know and trust someone before getting it on, no matter how long it’s been. But in my experience, anywhere from the 3rd to the 6th date tends to be the norm for people in their 30s, 40s and 50s, who form the bulk of my clientele. If the issue hadn’t at least been raised in conversation at that point, I’d suggest that’s the time to put it on the table.

5. Do people really get tested still?

People do get tested, but I’d say that it’s not something that is talked about in online dating profiles the way it was once listed in the personals at the back of NOW magazine. “Drug and disease free” is one of those phrases that, when I encounter it online, almost immediately tells me that this individual has been “out of the game” for some time. It’s dated. I hate to say it, but the public conversation about STIs has really stopped ever since HIV became a treatable chronic condition rather than a death sentence. However, it’s definitely conversation that still takes place in private. I recommend bringing it up once you’re ready to move beyond the kissing stage. The truth is that every single STI is treatable, and many, if treated, can no longer be communicated, so it shouldn’t a conversation to fear. It’s only a bad conversation if you have to divulge things after the fact. So get tested, get treated (if necessary), and be okay with asking. If they haven’t been tested recently, then use a condom.

6. How long should I wait to introduce my new love interest to my kids?

Another tough one, and very personal. I think if you’re someone to whom the idea of dating is a very big deal, then you should wait until you’ve been seeing the person for several months. In that scenario, I think you’d want to have at least a couple conversations about your expectations for the way they’re going to interact with your kids, and how they will be introduced.

That intoxicating first rush of a new love can sometimes blind you to a person’s faults, and if you meet a guy who later falls out of favour, you may regret having brought him into the situation for any number of reasons. But if your children regularly interact with your adult world, if they know your friends and your co-workers, then someone you’re dating is just another friend in the beginning. It won’t be a big deal to the kids unless you make it a big deal, so that’s what you really need to watch out for.

7. What are the pitfalls of getting back in the game when you have kids?

Underselling yourself is a problem. It’s unfortunate, but a lot of newly single parents feel their chances of finding romance are reduced simply because they have children. People will settle for the first person who expresses an interest, rather than being discerning and recognizing that they have a lot more options than they might think.

I can tell you from my own personal experience that I was never more popular in my life when I put myself out there after splitting with my son’s father. To the right sort of person, having kids is not the obstacle people think it is, particularly not online. Women right now have a better chance at finding love after kids than any time in history, yet there’s this sense of desperation that results in poor decision-making.

8. What are red flags to look for when starting to connect with someone new?

Online, the number one red flag for me is distance. If someone’s living in the Arctic Circle then sure, it’s probably advisable for them to cast as wide a net as possible geographically. But if you’re living in the GTA and getting inquiries from people in Florida, or Germany, or even Montreal, you should ask yourself why they’d be reaching out to you. I mean, we’re all special, but no stranger is 2000-miles-away special. I’d be questioning the motives of someone who wanted to begin a relationship on those terms.

Another warning sign is no profile pic. As I always tell my clients who are reluctant to post a photo, nothing screams “I’m married!” quite like the lack of a picture. If you’re worried about being recognized by someone you know, my response to that is, well what were they doing looking at a dating site? It’s nothing to be embarrassed about, but it’s also not the kind of thing people call each other out on, in my experience.

Other, more general things I’d be wary of include someone who never seems to bring up the next date, or won’t make concrete plans. You need to be with somebody who understands that moms with kids can’t “play it by ear” when it comes to getting together, and someone who never makes those moves but waits for you to ask may also not be as “into it” as you are.

If you’ve been dating someone for a while, like more than a month, and you’ve never been invited over, that’s another red flag for me. Are they married? Are they a hoarder? Do they live with four roommates they haven’t told you about? If they can only ever meet at your place or in public, that’s a clue that something is off.

And if anyone asks you to give or lend them money, or to invest in a business opportunity, you run, don’t walk, away from that person. That’s just not a normal dating interaction at any age or stage.

9. Online dating – what are the best sites out there to meet a normal person?

All the actual dating websites are full of normal people, with a sprinkling of what I’ll kindly call less traditional characters. But my favourites tend to be the big free sites: OkCupid, POF (Plenty of Fish), and Zoosk.

In my job, I’ll sometimes come across the same person’s profile on four or five different websites. You’re going to see individuals who use multiple websites to increase their visibility – and this is a practice I recommend.

I will say that I don’t personally recommend the dating apps, such as Tinder or Bumble, which have the ability to put you in immediate contact with a stranger. In my opinion, and my clients’ and friends’ experience, they’re really just for hookups. If that’s what you’re looking for, however, then by all means swipe right!

10. What are good ideas for a first date?

If you’ve met the person in a “real world” setting, then the first date is going to be more like a real date, and less of a getting-to-know-you session. You may have even already discussed what you’d like to do together – go for dinner, catch that play, or check out an art exhibit. Your thinking is going to be a little different than on a blind date, or with someone you’ve met online.

But since I’m usually setting up dates for people who have never met in real life, for me, it’s “anything but coffee.” I’ve actually blogged about why I think coffee is a lame first date – although I understand that it has many advantages. It’s cheap, there are cafés on literally every street corner these days, and who doesn’t love caffeine? But I suspect that part of the reason that so many first dates never result in second dates is that people are setting themselves up for failure by planning these very uninspiring get-togethers.

I like a moving first date, one that starts on its feet and keeps going, and if things go well, then maybe you end up sitting down to really have a conversation. So instead of saying “Meet me at the Starbucks,” it’s “meet me near the Starbucks,” and if the weather’s good, you choose a busy neighbourhood to walk around. You can get a lot more comfortable walking side-by-side with someone. You get a sense of their physicality. You see what they notice – are they people watchers? Do they comment on store windows? Fancy cars? A good busy neighbourhood is ideal for that sort of thing.

In smaller places, head to the cutest, oldest part of downtown, or even the Farmer’s Market. Street festivals are another great idea for that reason, or a park on a busy Saturday afternoon. Heck, I’ve even sent people to Costco on a first date! It’s perfect: you stroll around, there’s a ton of stuff to look at, and best of all, free samples! Just make sure one of you has a membership first.

As long as you choose a public place that’s relatively populous, you’re going to be safe, there’s going to be a lot of things to look at and talk about, and if things go well, there’s always a place to sit down and grab a coffee, or a drink, or a three-course-meal if you like each other enough.

Anne Marshall is a dating coach, writer, and matchmaker. As the Yenta-in-Chief of Junia Matchmaking Services, she’s helped dozens of couples find each other online, and form lasting bonds in the real world. View her recent interview on CBC here or visit Junia Matchmaking Services for more professional advice.