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13 Dating Tips For When You Want A Serious Relationship

Wait until you have real feelings before jumping into bed
by Cheekie Albay | Mar 29, 2018
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You’re done playing the field. You are a strong, independent hunk of a man with a good job and a penchant for flossing and any girl would be lucky to have you as long-term boo. But how do you move past the random hook-ups and “K lang” flings to finally finding the Beyoncé to your Jay-Z?

We talked to relationship coach Aileen Santos to gain tips on how to date once you’ve decided that you’re in it for the long haul. Read on for insights, and best of luck on the search, good sir.

1) Before bringing a woman into your life, get it together first

Santos emphasizes the need to have your life together before you start looking for a partner to share that life with. For her, this means “you know the direction you want to grow in, you are on track, and even though you’re still experiencing problems, you’re not overwhelmed by them or beaten up by them.”

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Furthermore, when you know the life you want for yourself, you would also know better what kind of partner would fit into that life. Otherwise, you’d be with someone just to be with someone—not exactly the healthiest reason for coupling up.

2) Refine your search to women who are more likely to be a match for you

Once you’ve gotten your shit together and are ready to meet prospects, make sure you do it in contexts where you are likely to find the best matches. If you are into entrepreneurship, join seminars and workshops attended by women with similar goals; if you are into active living, join gyms and activities that attract women passionate about the same things.

Similarly, when doing your stalking search on online platforms, go for women with whom you have mutual friends and shared interests, not the Australian swimsuit model who’s bound to leave your well-meaning message in her requests folder. FOREVER.

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3) Don’t make bars and clubs your hunting ground

Sorry, males prowling at watering holes: Santos isn’t too confident that you’ll find the love of your life there. 

“The location says nothing about the kind of person who goes in there except that they’re there to unwind and have a good time,” Santos explains. “The search is going to take much longer because you will not have anything in common to talk about that would be a basis for you to realize whether or not this person could be a good fit.”

4) Don’t knock the group date—light, worry-free meet-ups are ideal as initial dates

Sure, she looks hot in a sports bra and can carry on a conversation about intermittent fasting for at least three minutes, but before getting too excited by asking her out to dinner, slow your roll, lover boy.

“If you’re trying to get to know a woman and are really not sure yet, the best way to go about it is through group dates,” Santos recommends.

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You’ll have plenty of time to date her one-on-one once you’ve determined she’s GF material, so make the first hang a group hang where you can get better acquainted before making that unambiguous move.

5) Once you’ve determined her long-term potential, schedule that one-on-one date—but keep it breezy still

“For date number one, always have the mindset that it’s not a big deal; you are just getting to know her,” Santos advises. She recommends something casual like a coffee date, which keeps expectations low for the both of you, and using it as a chance to know her better rather than as an opportunity to bombard her with your unbridled attraction.

If you’re contemplating booking a fancy place for dinner complete with chauffeur service and you in a suit, DON’T. “Number one mistake guys make when they want to get in a relationship with a girl is they start with the grand gesture, and that’s so creepy,” Santos shares. “Grand gestures are for anniversaries, special occasions, or asking her if you can be a couple, but getting-to-know-you dates? No.”

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6) Lay off on the Jager shots at the start

We know, we know—the need for liquid courage is real when you’re trying to get up the nerve to talk to someone. But Santos warns against relying on it to facilitate one-on-one time because it paints a misleading picture of a person, seeing as “ninety-nine percent of the time you will be spending with this person if she ends up being your girlfriend is when she has not had drinks."

Plus, it makes you more likely to do stupid shit you’ll regret later on, so keep the drunken buffoonery for the bros.


7) In the beginning, always offer to foot the bill

This is pretty standard among guys on the first date, but as it turns out, this simple gesture serves a greater purpose in your budding bond than just saving her a few bucks.

According to Santos, offering to pay turns on different switches in a woman’s mind—the “he’s such a leader” switch, the “he’s such a gentleman” switch, and the “he’s interested in me” switch—which set you up as prime BF material in her twinkling eyes.

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8) Go on Date No. 2, but know the expectations that come with it

After that first date, you’ve decided you like her, so now what? Go for a second date, but caveat alert: “If it’s been more than two dates, there will already be expectations from women—not just from the woman herself, but from her friends who would most likely be planning your wedding already,” Santos says.

The same expectations apply for when you’re all up in her Messenger from morning ‘til night: She will assume you’re serious about her, and she wouldn’t be wrong to assume.

9) Pay special attention to: how she handles stress, and how she reacts when you’re stressed

Santos says that these situations are vital in providing insight into someone’s personality and whether or not you’d hit it off long-term. She warns against needy, clingy, or paranoid behavior, which are glaring red flags. “Sometimes men mistake someone who’s needy with good potential,” Santos says. “Men like feeling like the knight in shining armor.” 

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10) Avoid juggling prospects

While you’re not seeing anyone regularly, it’s fine to consider options, but like we said in #8, once you’ve been on the second date with a girl, she’s going to expect that you’re not out there sticking your business in every hole in sight. So keep the untargeted flirting to the getting-to-know-you stage, because if you keep at it even after you’ve built up a dating routine with someone, “you’re going to be seen as a player and that will destroy your chances,” Santos warns. 

11) Wait until you have real feelings before jumping into bed

This may be hard for you horndogs to accept, but it’s always best to be in love first before getting intimate. “A physical intimate relationship will mess up a lot of things if you don’t really know the person yet,” Santos says, pointing out how unreliable a shortcut it is to achieving emotional intimacy. “There’s that feeling of closeness, but it wears off, leaving a lot of questions afterward.”

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Santos advises holding off on sex until you’ve deepened your relationship, because “sex is going to be so much more special when you know that you are in it for the long haul.”

12) Once you’re sure about her, don’t waste time and DTR, baby

Once you’re sure about how you feel, there's no need to wait six months or follow some flimsy timeframe before defining the relationship. “If you know that she’s going to be a good match for you as a girlfriend, define it right away; express your serious intentions then and there,” Santos encourages.

Besides, you’ll have the rest of the boyfriend-girlfriend stage to figure out if you can get to the next level with her: tying the knot.

13) Remember: The only wasted opportunity is the one you don’t take

Sure, there’s always the chance that you’ll meet someone, realize it’s a big LOL NOPE after a few dates, and languish in her social media block list ‘til kingdom come, but that’s really the risk that comes with the search for a partner. 

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“A lot of people come to me and ask, ‘What if I’m wasting my time?’” Santos reveals. “Here’s what wasting time is: It’s when you know that you’ve actually met people that could’ve been worth it and you let those opportunities pass—that’s a wasted opportunity. Wasted opportunity is worse than wasted time. You get limited matches; you don’t always find people who could be a good match for you. And if you don’t take that risk, you not only waste time because you’re going to be spending time looking for other opportunities, but you will also have let go of that opportunity with that person.”

So go forth and take risks while trying not to be blocked by a scorned date, because once you do find the right person, those risks will all be worth it.

Have dating and relationship concerns? Contact relationship coach Aileen Santos at For more tips, watch her Fall in Love Friday episodes via or

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