Are you flirting with her or are you just being nice? 

Written by: Laura C. Anderson

I have this friend, Molly, who’s been seeing this guy she works with for a few weeks now. They’ve gone on three dates and she’s had a great time and believes her colleague, David, has as well. He’s doing everything right; he’s opening the car door, sending her ‘Goodnight’ texts, paying for their meals, complimenting her outfits, pulling out her chair, asking her about her likes and interests, etc.

But here’s the problem: David won’t make a move.

Molly says David flirts and he’s really nice but for whatever reason he won’t even hold her hand or kiss her. This makes Molly wonder if he’s even interested in pursuing her sexually or if he’s just enjoying time with a colleague outside of work? She came to me right away for my diagnosis and after talking to multiple men and women; we’ve decided David is suffering from Nice Guy Syndrome (Disclaimer: This is a completely made up term but since it sounds funny we're going to give it the acronym “NGS”).

According to Molly, David is the ‘nice guy’ around the office. He’s who everyone can count on to refill the copy machine or bring morning donuts to 6 AM meetings. He’s got a quiet demeanor about him making him oddly mysterious and sexy. It’s possible David is just such a good guy, he doesn’t want to make a move on Molly too soon because he doesn’t want to make her feel uncomfortable, or worst, get rejected.

Guys like David, if he is suffering from NGS, are typically not the assertive, dominant type to make the first move. If Molly bites the bullet and does what David isn’t ballsy enough to do, it may act as the springboard needed for their relationship to finally make it to first base. This way they can stop ending each meal with blue balls for dessert.

If you’re anything like me, you’re thinking he must be into her if he keeps asking her out and initiating the dates, right? Well here’s the thing - They began seeing each other outside of work after they both attended an office holiday party. After a few visits to the spiked punch bowl, a date for dinner was made. The only problem is – Molly can’t remember if she initiated the dinner or if David did. Not that it would otherwise matter if David had made a move by now. Because he hasn’t, Molly is worried she might make things awkward around the office if she keeps pursuing a guy who’s possibly made it clear isn’t interested in her in that way.

On her ride home from her last date she was mentally prepared to end things. Her confidence was rattled and she was tired of being mind-fucked. Is she reading the situation all-wrong and mistaking his niceness for wanting more? He keeps asking her out on dates, though, leading us to believe he’s interested, he just needs Molly to give him the O.K. to proceed without caution.

Girls are stubborn with making the first move but some guys just aren't assertive enough to move the relationship along. Although no one ever wants to be vulnerable, we recommend Molly get a beer in her, or a shot, perhaps even a Shirley Temple in hand, and just go for it. Kiss him. Anything. Because quite frankly she is dating a man with zero game – he is the Cleveland Brown of dating and she’s going to have to engage his body or do something to make it obvious it’s what she wants.

Molly’s situation has us wondering just how often are guys too nice to assert themselves and how often are they just downright not that into the girl? Below are some testimonials from girls who were eventually forced to make the first move. Some are happy they took the plunge while others wished they could crawl into a dark hole:


1. Happy I went for it.

“I have been dating the same guy for six years but during the first date I had to ask him if he wanted to hold my hand. I could tell he was really nervous and I was, too. Though other girls would probably be turned off by it, I thought it was endearing he was so shy.” Rian – 33

2. Read it all wrong. 

“I’m part of a co-ed kickball team where my teammates and I meet every Wednesday and Sunday for scrimmages and games. I noticed a really cute guy kept showing up to all the games, yet no one on my team knew who he was. I’d catch him eyeing me on the field and smiling at me when I looked over. It made it all so exciting! About a month later of him consistently showing up to my games I finally mustered up the confidence to walk over and tell him I’ve noticed him and I was flattered he kept watching me play. To that he answered, ‘Oh, I’m sorry, my boyfriend is your referee.’” – Leah, 27

3. Happy I went for it.

“I could tell the guy at Starbucks really wanted to ask me out because I got my coffee from him four mornings a week and it became something I think we both looked forward to. I would put extra effort into the way I looked on those days and he always acknowledged me in a more personal way than the other customers. For months we awkwardly smiled and flirted with each other for short spurts of time. He knew my order by heart and finally I just asked him out for coffee somewhere he wouldn't have to make it. He said yes and was so happy I asked because he wasn't sure if he could hit on me while on the clock.”  - Cassie, 23


4. Happy I went for it.

“I swiped with a guy on Tinder and we literally talked all day everyday THROUGH TINDER for two months before he finally gathered the nerve to ask me for my phone number so we could text. I joked with him that it took him long enough to ask and he apologized and said he didn't want to come off like every other guy and wanted me to know he truly was interested in getting to know my personality. I wasn't going to wait another two months for him to ask me out on a date so I asked him that night. We’ve been together for almost a year.” Rachael, 29

5. Read it all wrong.

“I work for an insurance company and one of our clients specifically requested me for a home visit after the interior of his home was damaged by a storm. I had made five or six house calls within a month for this guy and each time, he offered me food and drinks or asked if I needed to relax after my inspections. We seemed to have great chemistry and we were always making each other laugh. My work was finishing up so on my last visit I finally asked him out, figuring he was too shy to ask me. His face got deep red and he looked so uncomfortable. He politely thanked me for working so diligently on his home and said he only requested me because I had great reviews online. I left mortified to say the least.” Kate, 38

Laura C. Anderson | @s0mebl0nde



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