My very first date when I re-entered the dating scene as a single mother in my early 30s should have been a home run. He was a McDreamy-esque doctor with a son around the same age as mine. He was funny and kind as well as open to something serious.
But then we went out.
He was too self-deprecating. He kept making comments implying that he was ugly, which…isn’t necessarily what the woman who’s out on a date with you wants to hear.
He also didn’t seem to pick up on my physical flirtations. I brushed my hand against his as we were walking, but he didn’t try to hold my hand. After he walked me to my car, he stood stiffly in front of me and asked if he could kiss me.
Does he even…want to kiss me? I thought. I guess so if he’s asking…
“Sure,” I said. He chastely kissed me on the mouth, and we parted ways.
Unsurprisingly, we didn’t have another date, and I had several other one-date-wonders with men that, at least on paper, should have rocked my socks off.
If you’re a guy who keeps striking out on dates, you might need to follow some of the advice below.
1. Be your best self.
“Be yourself” is great advice, but if “be yourself” worked, you probably wouldn’t be reading a dating article right now. What that statement is missing is the word “best.” You want to be you, but the absolute best version of you.
People who are at their “best” have worked at overcoming their limitations and maximizing their strengths. They have goals, and they’re going for them. They’re comfortable with themselves and also take care of themselves. They bathe. They brush their teeth. They wear clothes that fit.
If you’re not feeling your best, she’s not going to feel you either.
Think about it: would you buy a TV from a salesman that said, “Meh, this one sort of sucks, but you’re here and it’s here, so you might as well buy it?”
If you’re unsure how to improve, here are some tips to help.
2. Kiss her early.
This may not work for every girl or for you, but every time a guy kissed me early, it helped to diffuse a later awkward AF situation by waiting until absolutely the last second.
For me, awkwardness kills sexy sexual tension. It imbues that time together with too much meaning (is he going to kiss me or not??), and one or both of you may walk away disappointed.
To relieve that pressure cooker, it can be different to try kissing her early, like thirty minutes or an hour into the date. If you’re laughing and she’s near you, just lean forward and plant your lips on hers and immediately go back to whatever you were talking about. A first kiss doesn’t have to be a big thing, and once you’ve gotten it out of the way, you can kiss her more later if she’s down.
3. Make it clear that you’re interested in her.
I once had a first date with a guy that left me feeling…meh. I thought we had a good conversation, and he was easy on the eyes, but I couldn’t get a read on him. I left the date confused whether he was interested in me or not.
When he contacted me for a second date, I was surprised, but I also wasn’t too keen on the idea. At the time, I was incredibly busy and the last thing I wanted to do was waste my time on someone who just sort of liked me.
“Hey, I’m just really busy right now, so I don’t think I’d be interested,” I responded.
“Please,” he texted back. “I think you’re exceptionally beautiful and really wanted to kiss you, but I was too nervous to do it.”
Where was this guy on our date??? I thought. I did give him a second chance, and we saw each other again later that week.
Unfortunately, date #2 wasn’t all that different from date #1. Good conversation, but it ran more like we were at a networking event (a lot of talk about our careers) than a date. None of the fun or flirtiness that might be expected on a date or with someone who genuinely wanted to bang me.
We kissed at the end of that date, but his lukewarm affect in person meant we didn’t go that far.
4. Be forthcoming.
A lot of men have received the dating advice, “Ask questions and listen.” The girl you’re out with is never going to learn anything about you if you don’t share anything about yourself. You also don’t want to just interrogate her.
When you ask her a question like, “What do you do?” share your answer afterward. Make it be a give and take. Hopefully, too, she’ll be asking you questions and moving the conversation along. If she’s not, it might be a sign she’s not into you.
5. Pay for her.
If you invited her out, you should offer to pay for her more often than not.
I understand that it’s the 21st century. I also understand that you never want to step on any toes in the #MeToo era, and you may have been coached to only pay for yourself.
But let’s be clear about some things: you want to make it clear that you’re on a date and not just going out as friends and that you’re not cheap. You convey that you’re interested and financially self-supporting by paying for the date.
No, you don’t have to be flashy with your money, and you shouldn’t be, but if your date is interested in a future with you, she’s going to want to know that you’re a guy who can take care of himself.
If a woman is trying to get you to pay for everything, that’ll be obvious (really, did she have to order two bottles of wine and the lobster??). If you aren’t into a woman going after you for your wallet, she won’t be a woman you’ll want to see again anyway.
If it’s within her means, a woman who values being your partner will offer to pitch in, cover the next date or round, etc.
Dating is already a grenade-laden experience. Don’t make a silly mistake and cut yourself out of the running before you’ve even gotten anywhere.
This post was previously published on Hello, Love.
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