Dating Advice: Should I have waited for him to pay for our first date?

Dear Guys,

Last night I went on a date and had a great time with a guy. When he stepped outside to smoke a cigarette I asked for the check and paid. I suppose I did this because I had a great time and wanted to avoid the awkwardness of the bill at the end.  I think my action backfired  because when he walked back in I think he was a little embarrassed to see I had paid and protested that he would have paid.

Did I make a crucial mistake by perhaps making him feel less masculine? (Though I acted fairly quickly and without too much contemplation.) Could this have been a deal breaker?


Dear Allie,

The simple answer is no. We don’t see how this would be a deal breaker, although, that depends on the guy. If he was also having a really good time, it’s more likely he just felt embarrassed. If he wasn’t having a good time, well, then it’s an easy excuse for him not to call you again.

Let’s back up. The timing of his cigarette break is throwing us a little. Although we don’t partake ourselves, we understand that some people like a smoke at the end of a meal. It’s possible he was weighing it in his mind and decided that it was better to excuse himself for a smoke then, instead of waiting and having to smoke in front of you. Still it seems like he could have figured out a better plan, seeing it was a first date, and the bill at the end of a first date can always be a little awkward.

This is not as bad as you think. If he treats it as a deal breaker, then rest assured, he wasn’t the guy for you. That would tell you that beneath his masculine front is an insecure guy. More likely, he’ll treat this as a great opportunity to wine and dine you on a second date. On his dime of course. (Hopefully you made it clear to him that you’d like to go out on a second date.)

One thing to think about: Relationships that work out, work out because the people want them to work out. Does that make sense? Meaning, initial awkwardness is never a deal breaker when two people like each other.

Keep us posted. We hope it works out for you.



Check out some of these other dating questions: 

Online dating; should I move forward? 

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Readers: Check out our “Relationship Memoirs”  page and read the latest contribution from Charlotte Pescale “Rebecca, a memoir.”


Hi Guys,

I have a first-date question… This is kind of similar to another question you just answered actually… but I still want your opinion lol. I met a guy really randomly a few weeks back— I was lost and asked him for directions, and we got to chatting briefly and we suggested going for coffee or drinks sometime and exchanged numbers. After that we texted pretty frequently. We did finally meet up last week —I think we were both a little drained. He was preparing for a conference that he was going away for this past weekend and I had a pretty busy day as well.

But the date went pretty well. (At least I think it did.) I was a bit nervous but I didn’t feel that “omg I need to get out of here” kind of feeling I’ve had on other dates! And I did notice subtle body language on his part that usually shows interest, like mimicking my own hand gestures, brushing my hand and that sort of thing. He was very attentive to what I was saying and I was attentive to what he was saying. But I was also nervous and when I’m nervous a part of me can err a little more to the stand-offish side rather than flirtatious.

At the end of the night (we hung out for at least three hours) he did walk me home but instead of trying to kiss me he gave me a friendly hug – but it was the one-arm hug! (The same hug we gave each other when we met up at the beginning of the night.) And when we said bye he said he’d let me know how his conference goes.

I was kind of confused because I thought the date went well and I didn’t pick up on any “he’s not interested” vibes so I was a little thrown off that he just said he’d let me know how it goes and not make even tentative plans for another date. I texted him the next day to say have a good weekend (conference was out of town) and he should’ve been back by tonight and I haven’t heard from him.

Usually if I don’t think a date went well I just walk away and say too bad, but he’s honestly the best guy I have met in a looooonng time and I’m reluctant to just walk away because I think I might have given off the “not-interested” vibes without meaning to. I figure he’s back in town now and I am not sure if I should text him asking him how it went? I don’t like initiating contact two times in a row but I’m wondering that if I did give off the wrong impression maybe that’s why he’s gone off the radar. But if I text him tomorrow or something asking him how it went would that just be really weird or would that maybe encourage him to at least talk to me again?? I can’t bring myself to totally walk away this time around but I also want to maintain some sort of dignity lol.



Dear Michelle, 

Ahh the ambiguity of the “one arm hug.” How wonderful. (We’re being sarcastic)

So we see your dilemma. Kind of. You see Michelle, if he has any sort of self-confidence, your “not interested” vibe would not be enough to dissuade him from getting back in touch with you. It’s not like you were acting that way when you first met him. You were actually out on a date, which means he must surmise that you were—or are—interested in him enough to spend more time with him than you actually needed to.

So we still think you need to let him take the initiative here. If he doesn’t get in touch with you in a week or so, feel free to text him then. But if we were in this situation, and we met a girl like you who we really liked, we’d definitely be looking forward to seeing you again. And we’d be contacting you as soon as we felt we could, especially being emboldened by your follow up text.

Be patient on this one. You don’t need to let it die, but you also don’t need to breathe life into it. It’s either going to happen or it’s not. And if he can’t see what’s in front of him, well then that’s his problem. Wait and week and then go from there.

We’re hoping this works out for you.

Take care,


ps. Feel free to ask us a follow question. Say hi to your friends up there in Canada. And check out our new “Relationship Memoirs” page. You might enjoy the latest contributions from Charlotte Pescale. “Rebecca, a memoir”

Online Dating: I ended the date early because I freaked out; but I really like him

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Online Dating Part 3: How to write a great written online profile  (Second example of BEFORE and AFTER version)


Dear Guys,

I met a guy on an online dating website. I’m not a fan of endless emails going back and forth so I suggested we meet up the following week after having exchanged a couple of emails and phone numbers. For your information, he contacted me first.

I gave him a choice of either Thursday or Friday for our first meeting and he chose Friday. Because he was new in town, he asked me to suggest a place to meet. So came Friday, I met him outside the bar we arranged to meet at. He was very friendly and gave me a big hug. We decided to go to a coffee shop and grab a coffee instead of staying at the bar because it was too crowded there. He was very gentlemanly and offered to pay for my coffee when he saw that I had my wallet in my hand. We talked over coffee. He told me about himself, why he was here, what he did. It turned out that he had a very successful career in finance. I was very nervous the whole time because to be honest, I don’t usually meet guys like that. He was good-looking, very fit, very smart, and very well-off. There were times when I really didn’t know what to say and I’m sure I sounded like my IQ had dropped by 20 points.

After the coffee, I thought he might’ve gotten so bored of me that he wanted to leave. To my surprise, he asked if I wanted to go to a bar and get a drink. I said okay but all the bars in the area were busy on Friday night so I suggested a place that was great for talking, if he didn’t mind walking for about 20 minutes. He said he didn’t mind at all so we walked for 20 minutes to a place near where I work. All the time we were talking—he made a lot of conversation even when I was nervous and didn’t know what to talk about.

So we went to this bar near where I worked. He ordered a drink for me, asking me if I wanted my “usual” which was one of the things I told him about earlier when we were having coffee. (That I usually only drink Vodka Diet Coke.) We sat down and started talking again. We talked about a lot of random things, he told me about his family, his job. He was definitely trying to impress me during the conversation. When the conversation stopped—usually when I was nervous I didn’t know what to say—he would look at me and smile.

I think the physical attraction and chemistry was definitely there. He was very gentlemanly throughout the whole night – steered away from topics of sex, when he talked he sometimes lightly touched my arms, although I could sense he was trying to be “cautious” with the amount of physical contact. He never had his phone out of his pocket, except when I went to the bathroom; when he saw me coming back he put his phone away immediately. At one point I asked him what he liked about my profile, immediately he looked shy and embarrassed and he said that I was very pretty and also I looked like an interesting person with lots of interests and hobbies. I asked him how he found me now that he’s met me in person, whether or not he found me boring, and he said no and that he was having a great time. Then he asked me what I liked about him.

When my glass of drink was almost empty he asked me if I wanted another one but because I was so nervous I said no. He got himself another drink and we kept talking. At that point I realized he was the kind of guy I had always dreamed of, but never got to meet. I felt like I was having a panic attack because I was worried I might blow it by not being myself and then appear boring to him. So when the conversation stopped again, and he did what he usually did when I wasn’t talking, which was staring into my eyes and smiling, I said awkwardly “I think I’d better get going.”  He looked really surprised and disappointed. It was the first time in the night that his smile disappeared from his face. But he just said, “Okay let’s go.”

By that time, we had spent a little over three hours together; it was 10 o’clock. Outside the bar, he asked me which way I was headed and I told him I was headed to the station opposite to where we came. He gave me a big hug and said, “I’ll give you a call and we’ll hang out again.”

The next day he sent me a text after midnight (Sunday morning) that said “Last night was fun. Glad I got to meet you. Hope we can see each other again soon.” I texted him back the next morning, eight hours later and said, “I had a lovely time too, thank you, and would love to catch up again. I’m sorry I left abruptly on Friday, I was not feeling very well and slightly nervous.”

Now it’s Tuesday night and he still hasn’t text me back or called me. What should I do? I definitely felt there was a lot of chemistry between us but I was also worried that because he was such a smart and successful guy, I might not sounded interesting or smart enough for him.

Should I contact him if he doesn’t get back to me? Is he interested but worried that I’m not interested in him? I think that by telling him I was nervous I was basically telling him that I liked him. Or is he just plain not interested enough to ask me out again?


Dear Chocobo,

Thanks for your question and for your donation.

All signs tell us this guy is into you, at least from what you describe of your first date. Lightly touching your arm, remembering your favorite drink, smiling during awkward pauses, telling you that he thought you were pretty, wanting to extend the night as long as he could, texting you to let you know he had a good time, are all very positive signs. He definitely seems attracted and interested in you. In general we don’t see any issues on his side, well, except the fact that he didn’t walk you to your car, train, or transportation. Maybe he was feeling rejected, but we like to see a guy insist even if he’s feeling insecure. (Just something we had to say.)

We know that you were nervous, especially when you realized this guy was the kind of guy you had always dreamed of, but you need to stop letting your insecurities show. Obviously he’s attracted to you because he contacted you, and because of all the positive signs we noted above. And if a guy is physically attracted to a woman he is willing to give it some time to see if he is into her in other ways. Meaning, your occasional loss of words is certainly not a deal breaker. However your insecurity could be if you’re not careful. Please don’t ask him again if you’re boring. Do you think you’re boring? Probably not, right? So don’t assume he does. Let him make his own mind up. Boring to one person, is interesting to another. It’s all subjective, so there’s no need to put that out there.

Just because he’s an interesting and smart guy doesn’t mean he’s looking for someone just like him. Have you heard of Howard Gardner’s Theory of Multiple Intelligences before? Basically Gardner says that people are smart in lots of different ways, and that there is not just one way to be smart. Just because this guy might know a lot about finance, or a variety of topics, and you don’t, doesn’t mean he’s smart and you’re not, or that you’re not good enough for him. If he judges you that way, then he’s not the kind of guy you want anyway.

“Chocobo,” just be yourself. That’s the most attractive quality a person can have. And frankly, you want him to fall for the person you are, not some projection of who you think he wants you to be.

Now to your questions. If he’s a confident guy he should contact you and ask you out again. You more than made up for your abrupt departure by letting him know you had a good time and telling him you were nervous. He should be able to pick up on that. If he doesn’t contact you this week, there’s nothing wrong with sending him another text saying you’d love to see him again. But we think you should wait it out this week. Text him next Monday.

One cautionary note: Hopefully he won’t wait until Thursday or later to ask you out for the weekend. He should be asking you out at least by Wednesday for a weekend date. Spur of the moment dates are great from Sun-Thurs, but not on a Friday and Saturday.

Chocobo—is that your nickname or a made up name?—we think you’ll get to see him again. Be patient. And hang in there. And please keep us posted. Please leave us a follow up comment—here in the comments section; we’ll respond here as well—or a follow up question if you see him again. Or ask us another question anytime.

Good luck,


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Dear Guys,

So I met an amazing guy. He is intelligent, funny, outdoorsy, in a band, all the things a girl could want. We met through mutual friends about two months ago and hit if off immediately. We stayed up the whole night going on randmon spontaneous adventures and ended up cuddling by the end.

Since then we have been seeing each other. (We have not talked about being exclusive). The dates have been great, creative, stimulating and I feel overall very comfortable with him and like him a lot. I fell asleep one night at his place early on, and since then we have been spending the night at each other’s places multiple times per week. We have fooled around but have not had sex yet.

Anyways, I am afraid maybe he is too into me and it makes me uncomfortable. He is a super energetic, friendly person so it his hard to tell if he is just his enthusiastic personality. I happen to know through friends that he liked me so much he was freaking out about what to do when he asked me out and he told everyone (friends, family) all about me right away. He left his pillow at my house— since I don’t sleep with one—and texts me everyday with random things and to see how I am. I have casually met his family, and when my parents were out of town for the holidays he invited me to his place. (I did not go, becuase it seemed too soon). He did get me a simple and thoughtful Christmas gift. He invited me to things a month in advance when we first started dating. He gives me space if I am busy or out with friends, and he certainly has his own busy life, but he wants to know everything about me, and I cannot shake the feeling that it is too intense. I have never really been in a relationship, so maybe it is just me?


Dear Kaitlin,

Thanks for your question.

So you need to ask yourself why this bothers you? Is it because in your heart of hearts you’re not sure you feel the same way about him? Or maybe you are a bit more cautious person and like to take things slowly? But from what you describe he sounds like a wonderful guy—the kind of person that everyone is looking for.

However, Kaitlin, just because he does so many wonderful things doesn’t mean he’s perfect for you. Love is a mystery. Sometimes we meet incredible people that we feel we should love, but there’s just no spark. Sometimes we get pressure from family and friends because they think a person is perfect for us, but for some reason they’re not. You are the only one who really knows how you feel.

Having said that, if it’s just your inexperience talking, or some other fear, maybe you can’t see the situation clearly. Maybe his intensity is clouding your perception of him. Here are the positive we see in him.

1. He is interested in everything about you. More than just sex.

2. He’s a solid communicator. Responsible. Follows through.

3. Positive person. Upbeat.

4. Independent person. Has his own life and gives you space.

5. Really cares about you.

6. Probably much more.

Kaitlin, believe it or not, guys are no different than girls when it comes to dating. When we meet someone we really like we get giddy, nervous, anxious, excited, silly, and yes, we even freak out. We ask our friends what to do, even though we know they won’t be much help. We try to figure out the best strategy to get the girl to go out on a date with us. Then we over plan and over think the first date. It’s quite amusing actually. But all of these intense feelings actually are good. Ask yourself: Do you really want to date a guy who just wants to hang out, watch movies, order Chinese, and then have sex? Do you really want a guy who tries to be Mr. Cool? Do you really want a guy who doesn’t call when he says he’s going to? And a guy who doesn’t want to know anything about you except your bra size? Think about it.

But we’ll finish our answer by coming back to what we said initially. It doesn’t matter how wonderful someone is on paper, you still need to feel those butterflies in your stomach. It’s up to you to figure that out. Just don’t let fear get in your way. He does sound like a solid guy. And be happy that he’s way into you. It’s so much better than the alternative.

Good luck. Feel free to ask us a follow up question, and definitely keep us posted. Leave us a comment here in the comments section and we’ll respond here as well.

Readers, please give your opinions as well!


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Domineering when I date: I give dating advice to men

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Hi There Guys,

I need some dating advice. It appears I’m quite domineering when I date men; I seem to be quick to tell a guy when he’s not doing things the right way. Or if he isn’t courting me at all, I tend to give them a mouthful. For example: I went on a date with a guy a week ago, he asked me out; when the bill arrived he refused to pay for it. I excused myself and went to the bathroom, and upon returning the bill was still sitting there. He then went to the bathroom, came back, and by that time I had asked the waitress to split the bill, so I could pay for myself. This guy says, “So you’re not paying for me?” To which I replied, “Hell no, pay for yourself!”

He made a few other jokes indicating that he was low status. He jokingly stated that he took the bus. The next day he texts me telling me he’s into and would like to see me again. I bluntly gave him dating advice. Some of which would easily blow a man’s ego to shreds. So my question is: How to I keep patient with men who are just so stupid? I feel like stupid men are everywhere? Or perhaps I’m just too domineering. Sometimes I feel like I’m actually doing a guy disservice by not saying anything. A clueless guy should know when he’s being clueless, so that he can apply new knowledge with future women. Perhaps other women can enjoy the fruits of my labor?

Any advice would help.

I’m actually a nice woman, so please be gentle with me.


ps. My other question has to do with how some guys act interested but then don’t organize the date, and put it on me to organize it, when they should be the ones doing it if they’re courting me?

Dear Sandy,

We don’t doubt you’re a very nice woman. Sure you may be a little domineering, but we think the real problem lies with the individual guys you’re dealing with. So our answer is more directed at the men out there, rather than you, or other women reading this.

First of all guys: If you ask a women out to dinner, expect to pay. In fact, you should insist on paying, unless for some reason you and your prospective date have had a conversation before you actually go out. And it’s our experience that if a woman insists on going “dutch” on a first date, she’s likely not interested in anything more than being friends. And guys, if you’re feeling broke, then don’t ask a woman to dinner. Take her out for lunch, or even coffee. If she likes you, she’ll be happy to spend time with you in any capacity.

Second of all guys: All the planning for your date falls on your shoulders. Women like to be surprised. (If it’s a good surprise of course.) But you get big points for being creative, or at least trying. If it doesn’t work out, then try laughing at yourself, which will be disarming, and come across as somewhat charming. (If you want to ask your prospective date for any particular type of food she doesn’t like that’s fine, but never put the burden of figuring out the evening on her. )

Sandy, we can see why acted the way you did, although most women probably would have grudgingly paid the bill and then vowed never to speak to the guy again. Sure you might be a bit more assertive than some, but we’d be just as annoyed by both of the scenarios you’ve painted for us.

Our advice is to keep being how you are. Maybe you’re helping these guys by speaking up about their behavior, but most likely they’re the kind of people that will deflect your barbs and assume it’s your problem. We suggest screening your potential dating candidates a little more closely before you agree to go out with them. Or maybe try meeting guys a bit more organically: Take a class, join a book group, go on a chartered travel vacation, or help out with some charity. There are a lot of different ways of meeting people, and doing something you care about will ensure that you’re meeting people with similar values.

Good luck,


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