Tips for Dating in Your Thirties

Dating as an adult is a lot harder than people realize. Here are some tips on how to thrive in the modern dating scene.
By aha insurance - Oct 23, 2018

At aha insurance we continually explore ways to stay in control of all aspects of life – because we know life is about more than insurance. In our Life Matters series we talk about staying in control of your life and living on your terms. Control feels great!

Dating in your thirties is not the same amusement park dating in your twenties was. Stakes are higher; perhaps you’re ready to settle down, maybe you want children, and you’ve probably had your heart broken a couple times already. It’s not easy when you’re looking for a meaningful relationship with the right person, so here are some great tips for dating in your thirties:

Know what you’re looking for, and make it about more than just attractiveness and/or money. Assuming you’ve had a couple relationships already, you probably now understand what kind of person you want to be involved with. Looks don’t last forever and money can come and go. A partner who is honest, hard-working, respectful, communicative and fun will build a happier future than most other qualities.

Dating in Your 30’s is More About Long-Term Compatibility

Know yourself too. Often people look for a laundry list of traits in others that may not always work well with their own characteristics. If you want someone who is a real go-getter, but you like to sleep until noon on weekends, rest assured Saturday and Sunday will become days of tension. Think about how the qualities you’re looking for will work with your own. Dating in your 30’s is more about long-term compatibility than a quick, good time.


Talk about past relationships – when it’s appropriate! It’s unreasonable to think you’ll never discuss past relationships, but timing is everything. Obviously first dates aren’t the time or place, and probably neither are the next few times you’re together. Wait until you’re in a meaningful relationship and having a relevant discussion about the topic before you start dishing about your romantic history, and always do so with respect. It’s okay to be honest about why a former relationship died, but calling exes derogatory names or exaggerating their negatives just reflects poorly on you.

Don’t leave your house looking like you just crawled out from under a rock. No, you don’t need full evening attire or fancy hair and make-up, but you never know who may find you attractive and smile at you over the grapefruits at the grocery store or sit beside you waiting at the dentist’s office. While romantic connections aren’t only about attraction, it’s still good to make an effort. Some of the greatest love stories have originated in the unique places and no, true love won’t see through your sloppy appearance.

Tech is Your Friend

Don’t be opposed to dating apps, even ones you pay for. We live in a digital age, so loving in a digital age isn’t so shocking anymore. Sites and apps that screen potential mates or attempt to match you based on information you provide might help you cut through all the noise. Just beware of those apps based 100% on appearance. Yes, you’d like someone you’re attracted to, but once you’re done expressing that attraction, you’ll eventually want to talk to the person also.

Don’t keep dating the wrong person. If you know there’s a “deal-breaker” in somebody’s personality and you see it after a couple dates, don’t continue to date that person. You’re not a kid anymore and you won’t change the person. On the other hand, don’t expect perfection, either. You’re not perfect so it’s hardly fair to expect others to uphold a higher standard.

Don’t fall in love on the first date, but don’t shut yourself off either. Sweeping romances were a part of what made your teens and twenties legendary, but now that you’re in your thirties, you need to take more control and have discerning tastes in who you fall in love with. Get to know somebody well enough to see some faults before you decide you’re in love. Conversely, don’t let any baggage from bad past relationships make you too closed to the possibility of falling in love.

Hooking Up is for 20-Somethings

Stop picking up in bars. No, seriously. That’s for the 20-somethings. Dating in your 30’s is about just that – dating. Getting to know people. Not a trail of quick hook-ups.

Be open to meeting new people. Blind dates may sound like a drag, but your friend or aunt is suggesting you meet that person for a reason. Go find out what that reason is. You don’t have to marry the person on the first date! Just make sure you have concrete exit strategies planned ahead of time in case you really can’t stand the person.

Avoid the Desperation Trap

Don’t sit around moping and waiting for someone else to fill the void in your life. Possible partners won’t find you intriguing if you’re not, and the smell of desperation comes across strong if you have nothing in your life but the relationship you’re trying to develop. Keep up with your favourite activities, start new ones, join clubs, play sports, spend time with family and friends, travel — just live a life where you feel fulfilled even without a romantic partner, and that’s usually when the right person comes along.

aha insurance is Canada’s first car and home insurance brokerage to offer a fully online customer experience. Customers can purchase and manage their car and home insurance online in minutes from the convenience of wherever they are. This puts customers in complete control, and control feels great.