Valentines Day Dilemma: I Am Dating Several Guys

If you are single and dating several people at once, Valentine’s Day can be fraught with fear of making the wrong move and losing a great opportunity to connect with the right mate.

Let me give you an example. My client Gail is dating several guys at once. She has just started dating most of these guys after the first of the year perhaps seeing them about two to four times each. She tells me she dreads Valentine’s Day and having to choose who she goes out with. And what if her first choice guy doesn’t ask her out? Does that take him out of the running completely?

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The only advantage you have this year is that Valentine’s Day is on a weekday and is not always convenient given work schedules. So you may not be asked out for February 14th , the actual Valentine’s Day but for the Saturday night on the weekend on the 16th.

Luckily for her, she has children and is spending the night with them. That gives her more latitude when one of her suitors asks her out. So who do you give your Saturday date night to?

It could be the first guy that asks you out since he is planning ahead and is respectfully asking you in advance. Or you could tell him you have plans and give him an alternative date if he is not your first or second choice.

And if he isn’t your top choice do you go out? Is there something that clearly tells you this down the list guy is not really for you? Or do you still would want to get to know him better and see what may develop?

At what point do you NOT schedule the Saturday night date night after Valentine’s Day? That is really up to you. However, my dating advice is if a guy is waiting to the last minute, you may not be his top choice or he may be the kind of guy who really doesn’t plan ahead. Are you okay with that? Some people are that way and some people aren’t. I’m a planner and that would drive me crazy so this would not be acceptable to me.

I would want the guy to ask ahead of time- by Tuesday or Wednesday at the very latest. If he really wants to pin me down for a date for the unofficial Valentine’s Day (Saturday, February 16th) then I would hope he would ask a week in advance.

My dating advice is if you just met someone online or at a social setting, I would reframe from going out with him or her this year for Valentine’s Day the 14th or the 16th. That puts too much pressure on the relationship and will not bode well for your future together. (Unless you both really feel that this is it!)

If asked, I would tell the man who asked, that you have plans with your family or girlfriends and that you would really like to see him another time. How about a Sunday brunch or afternoon activity?

How can you help yourself from feeling that Valentine’s Day is like musical chairs and that when the music stops, you have to have a date for Valentine’s Day (or the Saturday evening afterwards)?

My dating advice is to hold the holiday as a day to celebrate with a person you really care about – and just not a place holder. It’s better to be with a dear friend, your child or a group of singles who are out to have a good time than feeling uncomfortable with a guy who also feels uncomfortable and feels compelled to play up to the holiday.

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Remember, there is always next year!

What’s your dating advice on having a date for Valentine’s Day? What would you be inclined to do? And, what is the male perspective on this?