Ask Evie: I’m Newly Single After A Long-Term Relationship And I Need Help “Getting Back Into Dating”

Welcome to Ask Evie, our advice column. Readers can submit their questions, and our editors will dish out their best advice!

By Evie4 min read
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READER’S QUESTION: “I've been a longtime reader of Evie, and have been incorporating reading your articles every morning, especially since my breakup back in April. I was with this guy for 7 years, and it wasn't exactly the best relationship (hindsight is always 20/20).

But I just went on my first date last week since the break up and I realized how new and unfamiliar I am with the dating scene! I met this guy on Hinge, had a nice date, but I really wasn't interested in a 2nd one. It took SO much for me to mentally prepare me to even TEXT him that I wasn't interested. I also found I may have come off a bit too paranoid, as my taser was in full view for all to see. I also realized I wasn't sure what to do if we ran out of things to talk about or if he tried to make a move on me to go back to his place, if you know what I mean. I can understand saying something like ‘That's not really my style,’ but am really unsure on how to handle the situation if he's insistent. I'm definitely a people pleaser and I'm working on learning how to say ‘no.’

My main question is: Do you happen to have any tips for gals who are perhaps new to dating after a long-term relationship? How do we stay safe, assertive, and are presentable when we aren't really sure what ‘casual dating’ is these days? All advice for being newly single today are greatly appreciated!"

EVIE’S ADVICE: First of all, let’s keep in mind that it’s only been about three months since getting out of your last long-term relationship. You were with your boyfriend for seven years, so it’s totally understandable if you need to take a longer break before jumping back into the dating pool. Take this time to assess what went wrong on both sides and heal from what allowed you to stay in that bad relationship for so long. Feeling a little lost without him, even when you know it wasn’t the right relationship for you, is normal. Getting the help of an excellent counselor to assist you as you unpack your feelings and assess what you need to grow from that relationship in order to move forward is a great idea. 

We also recommend taking some time to journal and write down what kind of relationship you’re seeking, the qualities you’re looking for in a future husband, and the red flags you found in your past relationship that you don’t want to repeat. After you have all of these things figured out, you can go into your next date with clear standards and expectations to determine if it’s a good fit. Once you’re feeling more confident in yourself and sure of what you want out of your next relationship, dating should be less scary and stressful. 

Once you’re ready to enter into the dating world again, know that you definitely don’t need to conform to “casual dating” if that’s not what you want. Maybe meeting people through an app doesn’t feel romantic to you – that’s okay! Get more involved in your community or in church events, hit up a weekly gym class, or head to your local park with a girlfriend for the afternoon. You never know who you’ll meet “in the wild”; you could be standing right behind a handsome guy in line for coffee at your local cafe every morning not realizing you’re inches away from your future husband. Leave your phone in your pocket rather than scrolling social media while waiting or sitting at the park, and look around you. Strike up a conversation or smile and make flirty eyes if you cross paths with a handsome stranger. 

When it comes to meeting new people and setting firm, healthy boundaries, practice makes perfect. Remember, the right guy will respect your boundaries and the fact that you know what you want. Men are blunt and most prefer honesty and being upfront to playing games or trying to decipher your thoughts. Verbalize what you want and your intentions about the date. If you’re feeling uncomfortable with this at first, it’s a good idea to start the date by saying that you have plans afterwards at a specific time to give you an out. If you come across a guy who is offended by you upholding your standards or setting clear boundaries, that’s a major red flag, and it’s safe to say you can end the date knowing that you aren’t a good fit. 

Men are blunt and most prefer honesty and being upfront to playing games or trying to decipher your thoughts.

Now let’s chat about safety and feeling comfortable meeting a stranger. It’s completely normal to feel this way as a woman, and your fears are totally valid. There are a lot (we mean, a lot) of creeps out there. If your gut is telling you there is something off, listen to it. Never let politeness or fear of awkwardness or confrontation come in the way of protecting yourself. We have a few tips to set up the environment in a way that will add a layer of comfort and security to your date. A public restaurant or coffee shop at lunch time when there are plenty of other people around is a great idea. A daytime date also implicitly discourages "going back to his place" after the main event has ended. It’s always smart to drive separately on a first date so you don’t find yourself alone in a car with a total stranger. And make sure to tell a girlfriend or family member where you’ll be meeting your date, what time it’s expected to end, and that you’ll be checking in with them afterwards. Send them the address or drop a pin once you get to your location, and even consider sharing a screenshot of your date’s information (profile, photo, phone number, etc.) in the group text. This may sound like overkill, but it’s always better to be safe than sorry.

Now let’s assume that you’ve taken the time to heal from your past relationship, you’ve figured out exactly what you want, gotten comfortable with upholding your standards and setting healthy boundaries, and you’ve scheduled a first date in a location that feels safe to you. These are all great steps, but we’ll be honest with you… your date could still be a dud (and that’s okay!). You’re probably not going to stumble upon Prince Charming right away, so be patient and instead of adding that layer of pressure for the date to be perfect, just have fun with it! 

Think of your date as a fun meet up with free food and a chance to practice your flirting skills, or at the very least, a great story to share with your friends later. If the guy is interesting, respects your boundaries, and checks your boxes, great! Schedule a second date and see where it goes from there. If he’s totally lame or rude to the waitstaff, you got a free meal and a learning experience. Chances are, if you didn’t feel a connection, he probably didn’t either, so don’t feel bad letting him know that you aren’t interested in a second date. Don’t overthink it! Soon enough you’ll be snuggling on the couch with your husband, catching up on the latest Netflix series, and you’ll forget all about the weird, fun, and sometimes awkward dates that got you there. 

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